samarium

Summary

Summary: An element of the rare earth family of metals. It has the atomic symbol Sm, atomic number 62, and atomic weight 150.36. The oxide is used in the control rods of some nuclear reactors.

Top Publications

  1. Sartor O, Reid R, Bushnell D, Quick D, Ell P. Safety and efficacy of repeat administration of samarium Sm-153 lexidronam to patients with metastatic bone pain. Cancer. 2007;109:637-43 pubmed
    b>Samarium Sm 153 lexidronam (Sm-153) is an effective and well-tolerated treatment for painful bone metastases...
  2. Santos M, Furtado R, Konai M, Castiglioni M, Marchetti R, Natour J. Effectiveness of radiation synovectomy with samarium-153 particulate hydroxyapatite in rheumatoid arthritis patients with knee synovitis: a controlled randomized double-blind trial. Clinics (Sao Paulo). 2009;64:1187-93 pubmed publisher
    The aim of the present study was to investigate the effectiveness of Samarium(153)-particulate hydroxyapatite radiation synovectomy in rheumatoid arthritis patients with chronic knee synovitis.
  3. Sartor O, Reid R, Hoskin P, Quick D, Ell P, Coleman R, et al. Samarium-153-Lexidronam complex for treatment of painful bone metastases in hormone-refractory prostate cancer. Urology. 2004;63:940-5 pubmed
    A Phase III randomized trial was designed to assess the effectiveness of samarium-153 (153Sm)-lexidronam for palliation of bone pain in patients with hormone-refractory prostate cancer.
  4. Ferro Flores G, Ramírez F, Tendilla J, Pimentel González G, Murphy C, Meléndez Alafort L, et al. Preparation and pharmacokinetics of samarium(III)-153-labeled DTPA-bis-biotin. Characterization and theoretical studies of the samarium(III)-152 conjugate. Bioconjug Chem. 1999;10:726-34 pubmed
    ..Accordingly, the coordination sphere of Sm(III) was totally satisfied with nitrogen and oxygen donors; the best coordination number was 9. The conformation geometry of both compounds is presented...
  5. Ebran J, Jensen C, Johannesen S, Karaffa J, Lindsay K, Taaning R, et al. Creating carbon-carbon bonds with samarium diiodide for the synthesis of modified amino acids and peptides. Org Biomol Chem. 2006;4:3553-64 pubmed
    In this perspective, an overview of our experiences on the application of samarium diiodide in organic synthesis for the preparation of amino acid and peptide analogues is presented...
  6. Davies S, Rodriguez Solla H, Tamayo J, Cowley A, Concellon C, Garner A, et al. Asymmetric conjugate reductions with samarium diiodide: asymmetric synthesis of (2S,3R)- and (2S,3S)-[2-2H,3-2H]-leucine-(S)-phenylalanine dipeptides and (2S,3R)-[2-(2)H,3-2H]-phenylalanine methyl ester. Org Biomol Chem. 2005;3:1435-47 pubmed
    The highly diastereoselective samarium diiodide and D(2)O-promoted conjugate reduction of homochiral (E)- and (Z)-benzylidene and isobutylidene diketopiperazines (E)-5,7 and (Z)-6,8 has been demonstrated...
  7. Dolezal J, Vizda J, Odrazka K. Prospective evaluation of samarium-153-EDTMP radionuclide treatment for bone metastases in patients with hormone-refractory prostate cancer. Urol Int. 2007;78:50-7 pubmed
    ..exist: external-beam irradiation or intravenous administration of bone-seeking therapeutic radiopharmacon such as samarium-153-ethylene-diamino-tetramethylene-phosphonate (EDTMP)...
  8. Anderson P, Nunez R. Samarium lexidronam (153Sm-EDTMP): skeletal radiation for osteoblastic bone metastases and osteosarcoma. Expert Rev Anticancer Ther. 2007;7:1517-27 pubmed
    ..153)Samarium lexidronam ((153)Sm-EDTMP; Quadramet, Cytogen) is a radiopharmaceutical designed for deposition into bone ..
  9. Szostak M, Spain M, Procter D. Preparation of samarium(II) iodide: quantitative evaluation of the effect of water, oxygen, and peroxide content, preparative methods, and the activation of samarium metal. J Org Chem. 2012;77:3049-59 pubmed publisher
    b>Samarium(II) iodide (SmI(2)) is one of the most important reducing agents in organic synthesis. Synthetic chemistry promoted by SmI(2) depends on the efficient and reliable preparation of the reagent...

More Information

Publications62

  1. Attia M. Spectrofluorimetric assessment of Ramipril using optical sensor Samarium ion-doxycycline complex doped in sol-gel matrix. J Pharm Biomed Anal. 2010;51:7-11 pubmed publisher
    ..4x10(-9) - 1.0x10(-7)mol l(-1) and 2.4x10(-9) - 1.0x10(-7)mol l(-1) and detection limits of 6.0x10(-10) and 5.2x10(-10)mol l(-1), respectively...
  2. Serafini A. Therapy of metastatic bone pain. J Nucl Med. 2001;42:895-906 pubmed
  3. Beemelmanns C, Reissig H. Samarium diiodide induced ketyl-(het)arene cyclisations towards novel N-heterocycles. Chem Soc Rev. 2011;40:2199-210 pubmed publisher
    In this tutorial review we discuss recent advances in the field of ketyl-(het)arene cyclisations promoted by samarium diiodide and related processes...
  4. Chakraborty M, Wansley E, Carrasquillo J, Yu S, Paik C, Camphausen K, et al. The use of chelated radionuclide (samarium-153-ethylenediaminetetramethylenephosphonate) to modulate phenotype of tumor cells and enhance T cell-mediated killing. Clin Cancer Res. 2008;14:4241-9 pubmed publisher
    ..This study explored the possibility that exposure to palliative doses of a radiopharmaceutical agent could alter the phenotype of tumor cells to render them more susceptible to T cell-mediated killing...
  5. Ouadi A, Loussouarn A, Morandeau L, Remaud P, Faivre Chauvet A, Webb J, et al. Influence of trans-1,2-diaminocyclohexane structure and mixed carboxylic/phosphonic group combinations on samarium-153 chelation capacity and stability. Eur J Med Chem. 2004;39:467-72 pubmed
    ..Data on the stability of the best chelating agent compound 3: trans-cyclohexane-1,2-bis(aminomethylphosphonic)-N,N'-bis(ethyl-2-iminodiacetic acid) in human serum are presented...
  6. Edmonds D, Johnston D, Procter D. Samarium(II)-iodide-mediated cyclizations in natural product synthesis. Chem Rev. 2004;104:3371-404 pubmed
  7. Anderson P, Wiseman G, Erlandson L, Rodriguez V, Trotz B, Dubansky S, et al. Gemcitabine radiosensitization after high-dose samarium for osteoblastic osteosarcoma. Clin Cancer Res. 2005;11:6895-900 pubmed
    ..We sought to increase effectiveness of high-dose (153)Samarium ethylenediaminetetramethylenephosphonate (153Sm-EDTMP, Quadramet) on osteosarcomas using a radiosensitizer, ..
  8. Saadi J, Lentz D, Reissig H. Medium-sized carbocycles by samarium diiodide-induced carbonyl-alkene cyclizations. Org Lett. 2009;11:3334-7 pubmed publisher
    Intramolecular samarium diiodide-induced carbonyl-alkene or carbonyl-alkyne coupling reactions afforded without high dilution conditions 9- and 10-membered benzannulated carbocycles of type II and III in surprisingly good yields and ..
  9. Xu Q, Cheng B, Ye X, Zhai H. SmI(2)-mediated carbon-carbon bond fragmentation in alpha-aminomethyl malonates. Org Lett. 2009;11:4136-8 pubmed publisher
    A new and efficient samarium diiodide-promoted carbon-carbon bond fragmentation reaction of alpha-aminomethyl malonates, taking place normally at room temperature and generating the corresponding deaminomethylation products in 74-94% ..
  10. Dou G, Shi D. One pot synthesis of cis-bispyrimidodiazepinone derivatives via low-valent titanium reagent (TiCl4/Sm). Org Biomol Chem. 2011;9:7065-70 pubmed publisher
    ..The mechanistic course of the reaction suggests the involvement of reduction, coupling which determine the products' configuration and cyclization by one-pot...
  11. Marques F, Gano L, Paula Campello M, Lacerda S, Santos I, Lima L, et al. 13- and 14-membered macrocyclic ligands containing methylcarboxylate or methylphosphonate pendant arms: chemical and biological evaluation of their (153)Sm and (166)Ho complexes as potential agents for therapy or bone pain palliation. J Inorg Biochem. 2006;100:270-80 pubmed
    ..Thus, these studies support the potential interest of (153)Sm/(166)Ho-trita complexes for therapy when conjugated to a biomolecule and the potential usefulness of the (166)Ho-tritp complex in bone pain palliation...
  12. Johnston D, Couché E, Edmonds D, Muir K, Procter D. The first synthetic studies on pestalotiopsin A. A stereocontrolled approach to the functionalised bicyclic core. Org Biomol Chem. 2003;1:328-37 pubmed
    ..This constitutes the first synthetic studies on pestalotiopsin A. Our approach includes a samarium(II)-mediated 4-exo-trig cyclisation and a trans-lactonisation process triggered by the addition of alkylytterbium ..
  13. Guzmán Afonso C, González Silgo C, Torres M, Matesanz E, Mujica A. Structural anomalies related to changes in the conduction mechanisms of ?-Sm2(MoO4)3. J Phys Condens Matter. 2013;25:035902 pubmed publisher
    Polycrystalline samples of ?-phase samarium molybdate were prepared by solid-state synthesis and used for x-ray diffraction (from 300 to 1000 K) and dielectric spectroscopy (from 500 to 900 K and from 10(2) to 10(6) Hz)...
  14. Kamochi Y, Kudo T, Masuda T, Takadate A. Facile deoxygenation of dicarbonyl compounds using a samarium diiodide-additive system. Chem Pharm Bull (Tokyo). 2005;53:1017-20 pubmed
    The reduction of alpha- and beta-dicarbonyl compounds was investigated with samarium diiodide in the presence of additive...
  15. dos Santos M, Furtado R, Konai M, Castiglioni M, Marchetti R, Silva C, et al. Effectiveness of radiation synovectomy with Yttrium-90 and Samarium-153 particulate hydroxyapatite in rheumatoid arthritis patients with knee synovitis: a controlled, randomized, double-blinded trial. Clin Rheumatol. 2011;30:77-85 pubmed publisher
    The aim of the present study was to investigate the long-term effectiveness of and tolerance to Yttrium-90 and Samarium-153-particulate hydroxyapatite radiation synovectomy in patients with rheumatoid arthritis (RA) and chronic knee ..
  16. Donanzam B, Campos T, Dalmázio I, Valente E. Synthesis and characterization of calcium phosphate loaded with Ho-166 and Sm-153: a novel biomaterial for treatment of spine metastases. J Mater Sci Mater Med. 2013;24:2873-80 pubmed publisher
    ..Results showed bioceramics composed by multiphasic calcium phosphates along with holmium and samarium phosphates, with 8.9 and 13.7 % of Sm and Ho in weight, respectively...
  17. Vanzi E, Genovesi D, Di Martino F. Evaluation of a method for activity estimation in Sm-153 EDTMP imaging. Med Phys. 2009;36:1219-29 pubmed
  18. Dahlén A, Sundgren A, Lahmann M, Oscarson S, Hilmersson G. SmI2/water/amine mediates cleavage of allyl ether protected alcohols: application in carbohydrate synthesis and mechanistic considerations. Org Lett. 2003;5:4085-8 pubmed
    ..reaction: see text]. SmI2/H2O/amine provides selective cleavage of unsubstituted allyl ethers in good to excellent yields. This method is therefore useful in deprotection of alcohols and carbohydrates...
  19. Prabhakar G, Sachdev S, Umamaheswari S, Sivaprasad N, Bhatia M, Chaudhari P, et al. Development of samarium [32P] phosphate colloid for radiosynoviorthesis applications: preparation, biological and preliminary clinical studies experience. Appl Radiat Isot. 2007;65:1309-13 pubmed
    ..The results of clinical trials in humans are satisfactory and encouraging, satisfactory retention of the colloid in the knee joint and negligible leakage into the systemic circulation...
  20. Gu Q, Zheng Y, Li Y. Synthesis of 7-substituted-5-androstene derivatives promoted by SmI2. Steroids. 2006;71:96-101 pubmed
    ..The resulting 7alpha- and 7beta-isomers were carefully separated by column chromatography. The structural assignments of the 7alpha- and 7beta-isomers were determined by 13C-NMR...
  21. Morgans A, Smith M. Bone-targeted agents: preventing skeletal complications in prostate cancer. Urol Clin North Am. 2012;39:533-46 pubmed publisher
    ..ADT results in bone loss and fragility fractures. This review describes the biology of bone metastases, skeletal morbidity, and recent advances in bone-targeted therapies to prevent skeletal complications of prostate cancer...
  22. Janjetovic M, Träff A, Ankner T, Wettergren J, Hilmersson G. Solvent dependent reductive defluorination of aliphatic C-F bonds employing Sm(HMDS)2. Chem Commun (Camb). 2013;49:1826-8 pubmed publisher
    ..In n-hexane Sm(HMDS)(2) exhibits uniquely enhanced reductive ability towards the C-F bond compared to when using THF as solvent...
  23. Velasco Latrás M, Carreras Coderch L, Antoñanzas Villar F, Coya Viña J, Martín Comín J, Martínez Carderón F, et al. [Cost-effectiveness analysis of samario-153 (Quadramet) for the treatment of patients with prostate cancer and bone metastases]. Clin Transl Oncol. 2005;7:198-204 pubmed
    To evaluate the cost-effectiveness of samarium [153Sm-EDTMP] (Quadramet) compared to conventional therapy in the treatment of pain in patients with prostate cancer and bone metastases.
  24. Paquette L, Wah Lai K. Pinacol macrocyclization-based route to the polyfused medium-sized CDE ring system of lancifodilactone G. Org Lett. 2008;10:3781-4 pubmed publisher
    ..The polyfused medium-sized CDE ring system of lancifodilactone G is assembled via B-alkyl Suzuki-Miyaura cross-coupling and SmI 2-mediated pinacol macrocyclization as the key strategic steps...
  25. Lépy M, Amiot M, Bé M, Cassette P. Determination of the intensity of X- and gamma-ray emissions in the decay of 153Sm. Appl Radiat Isot. 2006;64:1428-34 pubmed
    ..Photon emission intensities have been derived for the main X- and gamma-rays, and the 103-keV emission has a measured intensity of (29.07 (20)) per 100 disintegrations...
  26. Yamashita M, Okuyama K, Kawasaki I, Nakamura S, Nagamine R, Tsujita T, et al. Reductive dimerization of alkylidenemalonates using samarium(II) diiodide and 1H-NMR behavior of the dimers, 2,3-diaryl-1,1,4,4-butanetetracarboxylates. Chem Pharm Bull (Tokyo). 2000;48:1799-802 pubmed
    ..Characteristic 1H-NMR behavior of the meso and racemic isomers is also discussed...
  27. Fani M, Vranjes S, Archimandritis S, Potamianos S, Xanthopoulos S, Bouziotis P, et al. Labeling of monoclonal antibodies with 153Sm for potential use in radioimmunotherapy. Appl Radiat Isot. 2002;57:665-74 pubmed
    ..leads to a labeling yield higher than 90%. Biodistribution studies in normal mice showed slow blood clearance and high uptake into the liver, kidney and lungs...
  28. Yang L, Tian W, Zhao Y, Jin X, Weng S, Wu J, et al. Sugar interaction with metal ions. The crystal structure and Raman spectra study of SmCl3-galactitol complex. J Inorg Biochem. 2001;83:161-7 pubmed
    ..The IR and Raman spectra of Pr-, Nd- and Sm-galactitol complexes are similar, which show that the three metal ions have the same coordination mode...
  29. Liu C, Wang J. Ultrasound-assisted synthesis of novel 4-(2-phenyl-1,2,3-triazol-4-yl)-3,4-dihydropyrimidin-(1H)-(thio)ones catalyzed by Sm(ClO(4))(3). Molecules. 2010;15:2087-95 pubmed publisher
    ..compounds, 2-phenyl-1,2,3-triazole-4-carbaldehyde and urea or thiourea under ultrasound irradiation and using samarium perchlorate as catalyst is described...
  30. Grobler J, Essen L, Williams R, Hurley J. C2 domain conformational changes in phospholipase C-delta 1. Nat Struct Biol. 1996;3:788-95 pubmed
    ..The distal sections of the C2 jaws move apart, opening the mouth by 9 A and creating a gap large enough to bind a phospholipid headgroup...
  31. Pell A, Pintacuda G, Emsley L. Single crystal nuclear magnetic resonance in spinning powders. J Chem Phys. 2011;135:144201 pubmed publisher
    ..Two formulations of this method are described and demonstrated with experimental examples on [1-(13)C]-alanine and the paramagnetic compound Sm(2)Sn(2)O(7)...
  32. Zhang L, Hu J, Chen J, Ding J. Nanostructured SmCo5 thin films with perpendicular anisotropy formed in a wide range of Sm-Co compositions. J Nanosci Nanotechnol. 2011;11:2644-7 pubmed
    ..The EDX result for this sample gives a composition of SmCo3Cu2.1 which confirms Cu diffusion into the SmCo5 layer. TEM image shows that SmCo5 film is well crystallized with a grain size of 50 nm...
  33. Yeong C, Abdullah B, Ng K, Chung L, Goh K, Sarji S, et al. Production and first use of 153SmCl3-ion exchange resin capsule formulation for assessing gastrointestinal motility. Appl Radiat Isot. 2012;70:450-5 pubmed publisher
    ..All the capsules remained intact in stomach. This proved to be a safe and practical oral capsule formulation for whole gut transit scintigraphy...
  34. Parmar D, Duffy L, Sadasivam D, Matsubara H, Bradley P, Flowers R, et al. Studies on the mechanism, selectivity, and synthetic utility of lactone reduction using SmI(2) and H(2)O. J Am Chem Soc. 2009;131:15467-73 pubmed publisher
    ..The cyclizations constitute the first examples of ester-alkene radical cyclizations in which the ester carbonyl acts as an acyl radical equivalent...
  35. Mooers B, Matthews B. Extension to 2268 atoms of direct methods in the ab initio determination of the unknown structure of bacteriophage P22 lysozyme. Acta Crystallogr D Biol Crystallogr. 2006;62:165-76 pubmed
    ..The presence of several partially occupied iodine anions and samarium cations augmented the ability of direct methods to locate all 2268 non-H protein atoms in the asymmetric unit, ..
  36. Yang H, Yu M, Jin H, Liu Z, Yao M, Liu B, et al. Isolation of three isomers of Sm@C84 and X-ray crystallographic characterization of Sm@D(3d)(19)-C84 and Sm@C2(13)-C84. J Am Chem Soc. 2012;134:5331-8 pubmed publisher
    ..and isolation of isomers of Sm@C(84) indicate that five different Sm@C(84) isomers have been found and that the source of samarium used for the generation of fullerene soot is important in determining which of these isomers form.
  37. Parmar D, Matsubara H, Price K, Spain M, Procter D. Lactone radical cyclizations and cyclization cascades mediated by SmI2-H2O. J Am Chem Soc. 2012;134:12751-7 pubmed publisher
    ..The cyclizations proceed by the trapping of radical anions formed by electron transfer reduction of the lactone carbonyl...
  38. Xu W, Niu B, Feng L, Shi Z, Lian Y. Access to an unexplored chiral C82 ?cage by encaging a divalent metal: structural elucidation and electrochemical studies of Sm@C2(5)-C82. Chemistry. 2012;18:14246-9 pubmed publisher
    Access to a chiral C(82) ?cage: Encaging a divalent samarium atom has provided access to an unexplored chiral cage of C(2)(5)-C(82) that has never been reported for trivalent M@C(82) or empty fullerenes...
  39. Szostak M, Spain M, Procter D. Selective synthesis of 3-hydroxy acids from Meldrum's acids using SmI2-H2O. Nat Protoc. 2012;7:970-7 pubmed publisher
    ..The protocol for selective monoreduction of Meldrum's acids takes ?6 h to complete...
  40. Li Q, Zuo W, Li F. Chelating ligand-mediated hydrothermal synthesis of samarium orthovanadate with decavanadate as vanadium source. ScientificWorldJournal. 2013;2013:127816 pubmed publisher
    A new ethylenediaminetetraacetic acid- (EDTA-) mediated hydrothermal route to prepare chrysanthemum-shaped samarium orthovanadate (SmVO?) nanocrystals with decavanadate (K?V??O??·9H?O) as vanadium source has been developed...
  41. Mittag T, Christensen K, Lindsay K, Nielsen N, Skrydstrup T. Direct entry to peptidyl ketones via SmI2-mediated C-C bond formation with readily accessible N-peptidyl oxazolidinones. J Org Chem. 2008;73:1088-92 pubmed publisher
    ..This method represents an alternative means for ligating two small peptides through a C-C bond-forming step...
  42. Williams D, Caddy J, Blann K. Highly functionalised cyclobutanols via samarium(II) iodide-induced pinacol cyclisations of carbohydrate-derived 1,4-diketones. Carbohydr Res. 2005;340:1301-9 pubmed
    ..These products can potentially be applied to the synthesis of anti-viral agents, some of whose structures incorporate chiral cyclobutanediol moieties...
  43. Szostak M, Spain M, Parmar D, Procter D. Selective reductive transformations using samarium diiodide-water. Chem Commun (Camb). 2012;48:330-46 pubmed publisher
    b>Samarium diiodide (SmI(2)) is one of the most important reductive electron transfer reagents available in the laboratory. Key to the popularity of SmI(2) is the ability of additives and co-solvents to tune the properties of the reagent...
  44. Fonseca K, Trindade B, Campos T. Development of a voxel model of the heart for dosimetry. Artif Organs. 2011;35:459-64 pubmed publisher
    ..The models are presented in two- and three-dimensional previews and the dosage profiles are shown by isodose curves superimposed onto the heart model...
  45. Collins K, Oliveira J, Guazzelli G, Sautier B, De Grazia S, Matsubara H, et al. Selective reductions of cyclic 1,3-diesters by using SmI(2) and H(2)O. Chemistry. 2010;16:10240-9 pubmed publisher
    ..Cyclization cascades are possible when two alkenes are present in the starting cyclic diester and lead to the formation of two rings and four stereocenters with excellent stereocontrol...
  46. Rai V, de Araujo C. Fluorescence intensity ratio technique for Sm3+ doped calibo glass. Spectrochim Acta A Mol Biomol Spectrosc. 2008;69:509-12 pubmed
    ..5nm line of Ar+ laser and inferred that the present system can be used as a temperature sensor...
  47. Tsuruta T. Selective accumulation of light or heavy rare earth elements using gram-positive bacteria. Colloids Surf B Biointerfaces. 2006;52:117-22 pubmed
    The accumulation of samarium from a solution only containing samarium by Arthrobacter nicotianae was examined. The amount of accumulated samarium was strongly affected by the concentration of samarium and pH of the solution...
  48. Mikkelsen L, Skrydstrup T. Synthesis of the C-linked disaccharide alpha-D-Man-(1-->4)-D-Man employing a SmI(2)-mediated C-glycosylation step: en route to cyclic C-oligosaccharides. J Org Chem. 2003;68:2123-8 pubmed
    ..The synthesis of the C4-formyl monosaccharide makes use of a stereoselective radical-based allylation followed by double bond migration and ozonolysis...
  49. Prata M, Santos A, Neves M, Geraldes C, de Lima J. (153)Sm(3+) and (111)In(3+) DTPA derivatives with high hepatic specificity: in vivo and in vitro studies. J Inorg Biochem. 2002;91:312-9 pubmed
  50. Zhang J, Guo J, Xiao H, Zhu L, Liu H, Zhang Y, et al. Simultaneous detection of different serum pepsinogens and its primary application. World J Gastroenterol. 2010;16:3072-7 pubmed
    ..To develop the simple, rapid and sensitive dual-label time-resolved fluoroimmunoassay for pepsinogens in human serum...
  51. Turner J, Chaudhary U. Dramatic prostate-specific antigen response with activated hemicellulose compound in metastatic castration-resistant prostate cancer. Anticancer Drugs. 2009;20:215-6 pubmed publisher
    ..We report on a 66-year-old gentleman with CRPC with an excellent serologic response to AHCC. This case hypothesizes that AHCC may have potential activity against CRPC...
  52. Assefa Z, Haire R, Raison P. Photoluminescence and Raman studies of Sm3+ and Nd3+ ions in zirconia matrices: example of energy transfer and host-guest interactions. Spectrochim Acta A Mol Biomol Spectrosc. 2004;60:89-95 pubmed
  53. Molander G, George K, Monovich L. Total synthesis of (+)-isoschizandrin utilizing a samarium(II) iodide-promoted 8-endo ketyl-olefin cyclization. J Org Chem. 2003;68:9533-40 pubmed
    The 13-step synthesis of (+)-isoschizandrin reported herein features a samarium(II) iodide-promoted 8-endo ketyl-olefin coupling to assemble the eight-membered ring present in the target concomitantly with the required functionality and ..