bridged ring heterocyclic compounds


Summary: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms.

Top Publications

  1. Sunderhaus J, Dockendorff C, Martin S. Applications of multicomponent reactions for the synthesis of diverse heterocyclic scaffolds. Org Lett. 2007;9:4223-6 pubmed
    ..This new approach to diversity-oriented synthesis was then applied to the first total synthesis of the isopavine alkaloid (+/-)-roelactamine. ..
  2. Achard M, Mosrin M, Tenaglia A, Buono G. Cobalt(I)-catalyzed [6+2] cycloadditions of cyclooctatetra(tri)ene with alkynes. J Org Chem. 2006;71:2907-10 pubmed
    ..Due to the valence tautomerism, 1,3,5-cyclooctatriene 2, in equilibrium with bicyclo[4.2.0]octa-2,4-diene A, and alkynes 3 are converted to 10 and 11 according to [6+2] and [4+2] cycloadditions, respectively. ..
  3. Mita N, Tamura O, Ishibashi H, Sakamoto M. Nucleophilic addition reaction of 2-trimethylsilyloxyfuran to N-gulosyl-C-alkoxymethylnitrones: synthetic approach to polyoxin C. Org Lett. 2002;4:1111-4 pubmed
    ..It was found that the selectivity was highly dependent on the bulkiness of the C-substituent of the nitrone. The major adducts were elaborated into the key intermediate of polyoxin C. ..
  4. Hirai G, Oguri H, Hayashi M, Koyama K, Koizumi Y, Moharram S, et al. Synthesis and preliminary biological evaluation of truncated zoanthenol analogues. Bioorg Med Chem Lett. 2004;14:2647-51 pubmed
    ..A preliminary SAR study suggested that the hydrochloride of the CEFG-ring portion is an active pharmacophore for suppressing the growth of interleukin-6-dependent MH60 cells. ..
  5. Kalinin A, Chauder B, Rakhit S, Snieckus V. seco-C/D ring analogues of ergot alkaloids. Synthesis via intramolecular Heck and ring-closing metathesis reactions. Org Lett. 2003;5:3519-21 pubmed
  6. Caspi D, Garg N, Stoltz B. Heterogeneous reductive isomerization reaction using catalytic Pd/C and H2. Org Lett. 2005;7:2513-6 pubmed
    ..Mechanistic studies suggest that this reaction does not proceed via a stepwise reduction/elimination sequence or a pi-allylpalladium intermediate. ..
  7. Grabner S, Modec B, Cemazar M, Bukovec N. Crystal structures and cytotoxicity of isopropylamine Pt(II) complexes: a trinuclear squarato-bridged [Pt3(mu2-C4O4)3(H2NPri)6].3H2O and a mononuclear cis-[Pt(NO3)2(H2NPri)2]. J Inorg Biochem. 2005;99:1465-71 pubmed
  8. Santana M, Garcia G, Lozano A, López G, Tudela J, Perez J, et al. Pentacoordinate nickel(II) complexes double bridged by phosphate ester or phosphinate ligands: spectroscopic, structural, kinetic, and magnetic studies. Chemistry. 2004;10:1738-46 pubmed
    ..The proposed mechanism for TNP-promoted hydrolysis can be described as one-substrate/two-product, and can be fitted to a Michaelis-Menten equation. ..
  9. Kanchanapoom T, Kasai R, Chumsri P, Yamasaki K. Quassinoids from Eurycoma harmandiana. Phytochemistry. 2001;57:1205-8 pubmed
    ..The structural elucidations were based on analyses of spectroscopic data. ..

More Information


  1. Solé D, Urbaneja X, Bonjoch J. Synthesis of the 4-azatricyclo[,8)]undecan-10-one core of daphniphyllum alkaloid calyciphylline A using a Pd-catalyzed enolate alkenylation. Org Lett. 2005;7:5461-4 pubmed
  2. Yamazaki S, Morikawa S, Miyazaki K, Takebayashi M, Yamamoto Y, Morimoto T, et al. Zinc-catalyzed reactions of ethenetricarboxylates with 2-(trimethylsilylethynyl)anilines leading to bridged quinoline derivatives. Org Lett. 2009;11:2796-9 pubmed publisher
    ..The reaction of 1b with 2'-aminoacetophenone also gave the bridged quinoline derivative in 41% yield. Thermal reaction of bridged quinolines (180-190 degrees C) afforded indole derivatives in moderate to good yields. ..
  3. Pearson W, Mans D, Kampf J. Cycloadditions of 2-azaallyllithium species with conjugated polyenes. J Org Chem. 2004;69:1235-47 pubmed
    ..The cycloadducts derived from cyclic 2-azaallyllithium species possess the 7-azabicyclo[2.2.1]heptane (tropane) or 8-azabicyclo[3.2.1]octane ring system and have been elaborated into cocaine-like analogues. ..
  4. Zhang L, Wang Y, Buckingham C, Herndon J. Synthesis of furan-bridged 10-membered rings through [8 + 2]-cycloaddition of dienylfurans and acetylenic esters. Org Lett. 2005;7:1665-7 pubmed
    ..Dienylfuran intermediates were generated using either a chromium carbene-based method or aldol-based methods. Reaction of [8 + 2]-cycloadducts with electrophilic reagents occurred selectively at the enol ether alkene. ..
  5. Denmark S, Gomez L. Tandem double intramolecular [4+2]/[3+2] cycloadditions of nitroalkenes. The fused/bridged mode. J Org Chem. 2003;68:8015-24 pubmed
    ..This method converts linear polyenes to functionalized polycyclic systems bearing up to six stereogenic centers. ..
  6. Sugano N, Koizumi Y, Hirai G, Oguri H, Kobayashi S, Yamashita S, et al. Enantioselective synthesis of the fully functionalized ABC ring of zoanthenol. Chem Asian J. 2008;3:1549-57 pubmed publisher
    ..The key features of the synthesis are the enzymatic kinetic optical resolution and the Mizoroki-Heck/Simmons-Smith reaction strategy used to construct the congested asymmetric quaternary carbons. ..
  7. Pearson W, Stoy P, Mi Y. A three-component, one-pot synthesis of indolizidines and related heterocycles via the [3+2] cycloaddition of nonstabilized azomethine ylides. J Org Chem. 2004;69:1919-39 pubmed
    ..The same (2-azaallyl)stannanes may be transmetalated by n-butyllithium to generate 2-azaallyllithiums, which also may undergo a [3+2] cycloaddition/N-alkylation cascade to form indolizidines. ..
  8. Wang G, Vedejs E. Stereocontrol in N-directed hydroboration: synthesis of amino alcohols related to the piperidine alkaloids. Org Lett. 2009;11:1059-61 pubmed publisher
    ..Comparisons with acyclic model structures show that the source of regiocontrol with the terminal alkene is due to a steric effect of the axial piperidine C(3,5) hydrogens that destabilize the competing bridged bicyclic transition state...
  9. Mishra L, Vilaplana R, Singh V, Yadaw A, Gonzalez Vilchez F. Nitrate/nitrite reductase activity of sulfido/selenido bridged dinuclear ruthenium(III) complexes. J Inorg Biochem. 2001;86:581-5 pubmed
    ..The electrochemical behaviour of the complexes showed irreversible oxidation peaks at +(1.04-1.40) V quite comparable to those reported for sulphido bridged complexes. ..
  10. Cheng X, Waters S. Concise total syntheses of the Lycopodium alkaloids (+/-)-nankakurines A and B via luciduline. Org Lett. 2010;12:205-7 pubmed publisher
    ..Key features include a short preparation of luciduline followed by a concise and stereoselective aminoallylation/ring-closing metathesis protocol to fashion the spiropiperidine ring common to nankakurines A and B. ..
  11. Kossakowski J, Wojciechowska A. Synthesis of oxiran-2-ylmethyl and oxiran-2-ylmethoxy derivatives of some 4-azatricyclo[,6)]dec-8-ene-3,5-diones as potential beta-adrenolytics. Acta Pol Pharm. 2006;63:485-90 pubmed
    ..2.1.0(2,6)]dec-8-ene-3,5-dione have been prepared. The pharmacological profile of selected compounds was evaluated for their affinities at beta-adrenoceptors. The investigated compounds exhibit modest affinity for these receptors. ..
  12. Bunnelle W, Daanen J, Ryther K, Schrimpf M, Dart M, Gelain A, et al. Structure-activity studies and analgesic efficacy of N-(3-pyridinyl)-bridged bicyclic diamines, exceptionally potent agonists at nicotinic acetylcholine receptors. J Med Chem. 2007;50:3627-44 pubmed
  13. Fitch R, Spande T, Garraffo H, Yeh H, Daly J. Phantasmidine: an epibatidine congener from the ecuadorian poison frog Epipedobates anthonyi. J Nat Prod. 2010;73:331-7 pubmed publisher
    ..After synthesis, this novel rigid agonist may serve as a selective probe for beta4-containing nicotinic receptors and potentially lead to useful pharmaceuticals. ..
  14. Cabrera G, Butler M, Rodriguez M, Godeas A, Haddad R, Eberlin M. A sorbicillinoid urea from an intertidal Paecilomyces marquandii. J Nat Prod. 2006;69:1806-8 pubmed
    ..The absolute stereochemistry was deduced by comparison of the CD curves with those of known members of the bisorbicillinol family. This is the first report of the isolation of a ureido sorbicillinol derivative. ..
  15. Martinez Junza V, Rizzi A, Jolliffe K, Head N, Paddon Row M, Braslavsky S. Conformational and photophysical studies on porphyrin-containing donor-bridge-acceptor compounds. Charge separation in micellar nanoreactors. Phys Chem Chem Phys. 2005;7:4114-25 pubmed
    ..The data obtained with the more flexible "supermolecule" 2 showed the predicted large conformation flexibility of these molecules. ..
  16. Tang Q, Yang C, Liu J, Ye W, Zhao S, Lu Y, et al. [A new hetisine-type alkaloid from the stems and leaves of Aconitum coreanum]. Yao Xue Xue Bao. 2005;40:640-3 pubmed
    ..The new alkaloid was identified on the basis of spectral analysis. Two compounds were isolated and identified as: 13-dehydro-1beta-acetyl-2alpha,6beta-dihydroxyhetisine (I) and Guanfu base G (II). Compound I is a new alkaloid. ..
  17. Jayasuriya H, Guan Z, Dombrowski A, Bills G, Polishook J, Jenkins R, et al. Isolation, structure, and coccidiostat activity of coccidiostatin A. J Nat Prod. 2007;70:1364-7 pubmed
    ..The isolation, structure elucidation, relative configuration, and activity of coccidiostatin A (2) are described. ..
  18. Edwards D, Pritchard R, Wallace T. Fine-tuning of biaryl dihedral angles: structural characterization of five homologous three-atom bridged biphenyls by X-ray crystallography. Acta Crystallogr B. 2005;61:335-45 pubmed
  19. Bertolini T, Nguyen Q, Harvey D. Construction of [4.3.1]propellanes via molybdenum fischer carbene complexes. J Org Chem. 2002;67:8675-8 pubmed
    ..The range of dienyne substrates that participate in this reaction is explored and its mechanism is analyzed and discussed. ..
  20. Behenna D, Stockdill J, Stoltz B. Synthesis of the carbocyclic core of zoanthenol: implementation of an unusual acid-catalyzed cyclization. Angew Chem Int Ed Engl. 2007;46:4077-80 pubmed
  21. Machocho A, Kiprono P, Grinberg S, Bittner S. Pentacyclic triterpenoids from Embelia schimperi. Phytochemistry. 2003;62:573-7 pubmed
    ..Three of the triterpenoids exhibited mild antibacterial properties against the gram-positive bacterial strain Rhodococcus sp...
  22. Castro Rodriguez I, Olsen K, Gantzel P, Meyer K. Uranium tris-aryloxide derivatives supported by triazacyclononane: engendering a reactive uranium(III) center with a single pocket for reactivity. J Am Chem Soc. 2003;125:4565-71 pubmed
    ..The magnetism of the series of complexes with an [N3O3-N(ax)] core structure and oxidation states +III, +IV, and +V is discussed in context of the electronic structures. ..
  23. He H, Pei B, Chou H, Tian T, Chan W, Lee A. Camphor sulfonyl hydrazines (CaSH) as organocatalysts in enantioselective Diels-Alder reactions. Org Lett. 2008;10:2421-4 pubmed publisher
    ..With trichloroacetic acid as cocatalyst, they are efficient organocatalysts for enantioselective Diels-Alder reactions with good chemical yields and up to 96% ee. The reactions took place in brine at 0 degrees C to room temperature. ..
  24. González Gálvez D, Garcia Garcia E, Alibés R, Bayón P, de March P, Figueredo M, et al. Enantioselective approach to Securinega alkaloids. Total synthesis of securinine and (-)-norsecurinine. J Org Chem. 2009;74:6199-211 pubmed publisher
    ..Moreover, since the enantioselectivity was originated by a chiral phosphine ligand, the antipode of which is readily available, the same route is expected to give access to (+)-norsecurinine and virosecurinine. ..
  25. Bardají G, Cantó M, Alibés R, Bayón P, Busqué F, de March P, et al. Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide. J Org Chem. 2008;73:7657-62 pubmed publisher
    ..Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide. ..
  26. Liu P, Hong S, Weinreb S. Total synthesis of the Securinega alkaloid (-)-secu'amamine A. J Am Chem Soc. 2008;130:7562-3 pubmed publisher
    ..In addition, 1H NMR NOE studies and X-ray analysis on the synthetic alkaloid have established that the indolizidine moiety is trans-fused. ..
  27. Ohsaki A, Kobayashi Y, Yoneda K, Kishida A, Ishiyama H. Securinega alkaloids from the wood of Securinega suffruticosa var. amamiensis. J Nat Prod. 2007;70:2003-5 pubmed
    ..amamiensis, together with five known analogues ( 4, 6- 9). The structures 1- 3 were elucidated by spectroscopic methods including 2D NMR, and all eight compounds were evaluated for cytotoxicity against two cancer cell lines. ..
  28. Szostak M, AUBE J. Direct synthesis of medium-bridged twisted amides via a transannular cyclization strategy. Org Lett. 2009;11:3878-81 pubmed publisher
    ..The sequential RCM to construct a challenging medium-sized ring followed by a transannular cyclization across a medium-sized ring delivers previously unattainable twisted amides from simple acyclic precursors. ..
  29. Nilsson B, Overman L, Read de Alaniz J, Rohde J. Enantioselective total syntheses of nankakurines A and B: confirmation of structure and establishment of absolute configuration. J Am Chem Soc. 2008;130:11297-9 pubmed publisher
    ..The syntheses are sufficiently concise that gram quantities of (+)-nankakurine A (2) and (+)-nankakurine B (3) will be available for further biological studies. ..
  30. Han Y, Giragossian C, Mierke D, Chorev M. Ni-to-Ni+ 3-ethylene-bridged partially modified retro-inverso tetrapeptide beta-turn mimetic: design, synthesis, and structural characterization. J Org Chem. 2002;67:5085-97 pubmed
  31. Hirai G, Koizumi Y, Moharram S, Oguri H, Hirama M. Construction of the benzylic quaternary carbon center of zoanthenol by intramolecular Mizoroki-Heck reaction of enone. Org Lett. 2002;4:1627-30 pubmed
    ..The cis B/C ring system was stereoselectively converted to the trans-fused framework through a SmI2-promoted deoxygenation of the alpha-hydroxy ketone. ..
  32. Hirasawa Y, Morita H, Kobayashi J. Nankakurine A, a novel C16N2-type alkaloid from Lycopodium hamiltonii. Org Lett. 2004;6:3389-91 pubmed
    ..3.1]nonane ring connected to a piperidine ring through a spiro carbon, was isolated from the club moss Lycopodium hamiltonii. The structure and relative stereochemistry were elucidated on the basis of spectroscopic data. ..
  33. Saulnier M, Langley D, Frennesson D, Long B, Huang S, Gao Q, et al. Novel 3',6'-anhydro and N12,N13-bridged glycosylated fluoroindolo[2,3-a]carbazoles as topoisomerase I inhibitors. Fluorine as a leaving group from sp3 carbon. Org Lett. 2005;7:1271-4 pubmed
    ..A novel N12,N13-bridged sugar analogue 2 results from loss of 4'-fluorine from beta-N-glycosylated analogue 4. Both analogues 1 and 2 display topo I inhibitory potencies similar to camptothecin. ..
  34. Nelson H, Stoltz B. Progress toward the synthesis of the basiliolides and transtaganolides: an intramolecular pyrone Diels-Alder entry into a novel class of natural products. Org Lett. 2008;10:25-8 pubmed
    ..A highly endo-selective intramolecular pyrone Diels-Alder (IMPDA) cycloaddition rapidly constructs the tricyclic core of the basiliolides and transtaganolides. ..
  35. Magnus P, Padilla A. Proposed biogenetic origin of secu'amamine A from allosecurinine: a model study to support the intermediacy of the putative aziridinium ion. Org Lett. 2006;8:3569-71 pubmed
    ..reaction: see text] A model study to support the intermediacy of the aziridinium ion in the proposed biogenetic origin of secu'amamine A from allosecurinine is described. ..
  36. Marrero J, Rodriguez A, Barnes C. Intricarene, an unprecedented trispiropentacyclic diterpene from the Caribbean Sea plume Pseudopterogorgia kallos. Org Lett. 2005;7:1877-80 pubmed
    ..The unprecedented carbon skeleton of 1 constitutes a new addition to the already impressive architectural diversity of the diterpene class of marine secondary metabolites. ..
  37. Bunyapaiboonsri T, Yoiprommarat S, Intereya K, Rachtawee P, Hywel Jones N, Isaka M. Isariotins E and F, spirocyclic and bicyclic hemiacetals from the entomopathogenic fungus Isaria tenuipes BCC 12625. J Nat Prod. 2009;72:756-9 pubmed publisher
    ..1 microM and cytotoxic activities against cancer cell lines (KB, BC, and NCI-H187) and nonmalignant (Vero) cells with respective IC(50) values of 15.8, 2.4, 1.6, and 2.9 microM. ..
  38. Chauke V, Matemadombo F, Nyokong T. Remarkable sensitivity for detection of bisphenol A on a gold electrode modified with nickel tetraamino phthalocyanine containing Ni-O-Ni bridges. J Hazard Mater. 2010;178:180-6 pubmed publisher
    ..The poly-70-Ni(OH)TAPc modified electrode could reliably detect bisphenol A in a concentration range of 7x10(-4) to 3x10(-2)mol L(-1) with a limit of detection of 3.68x10(-9)mol L(-1). The sensitivity was 3.26x10(-4)A mol(-1) L cm(-2). ..
  39. Kakehi A, Suga H, Okuno H, Okuhara M, Ohta A. Preparation of new nitrogen-bridged heterocycles. 60. Syntheses and conformational analyses of bis(indolizin-1-yl) disulfides. Chem Pharm Bull (Tokyo). 2007;55:1458-65 pubmed
    ..These three types of gauche structures were confirmed by X-ray analyses. ..
  40. Dyatkin A, Hoekstra W, Hlasta D, Andrade Gordon P, de Garavilla L, Demarest K, et al. Bridged bicyclic vasopressin receptor antagonists with V(2)-selective or dual V(1a)/V(2) activity. Bioorg Med Chem Lett. 2002;12:3081-4 pubmed
    ..g., 5) and balanced dual V(1a)/V(2) (e.g., 10) compounds. Data from receptor binding, cell-based functional, and in vivo assays are presented [corrected] ..
  41. Coucouvanis D, Han J, Moon N. Synthesis and characterization of sulfur-voided cubanes. Structural analogues for the MoFe(3)S(3) subunit in the nitrogenase cofactor. J Am Chem Soc. 2002;124:216-24 pubmed
    ..On the basis of this argument, a possible N(2)-binding and reduction mechanism on the FeMoco-cofactor is proposed. ..
  42. Leduc A, Kerr M. Total synthesis of (-)-allosecurinine. Angew Chem Int Ed Engl. 2008;47:7945-8 pubmed publisher
  43. Pearson W, Mans D, Kampf J. Cycloadditions of nonstabilized 2-azaallyllithiums with cycloheptatriene. Org Lett. 2002;4:3099-102 pubmed
    ..The peri- and stereoselectivity of this process are discussed. ..
  44. Muthusamy S, Babu S, Gunanathan C, Ganguly B, Suresh E, Dastidar P. Tandem cyclization-cycloaddition behavior of rhodium carbenoids with carbonyl compounds: stereoselective studies on the construction of novel epoxy-bridged tetrahydropyranone frameworks. J Org Chem. 2002;67:8019-33 pubmed
    ..The calculations further revealed that a severe steric interaction caused by the phenyl rings present in dipolarophile 34 with dipole 14a increases the activation barrier of the transition state during the cycloaddition process. ..
  45. Solé D, Serrano O. Palladium-catalysed synthesis of 1-isoindolecarboxylic acid esters and sequential Diels-Alder reactions: access to bridged- and fused-ring heterocycles. Org Biomol Chem. 2009;7:3382-4 pubmed publisher
  46. Yao L, AUBE J. Cation-pi control of regiochemistry of intramolecular schmidt reactions en route to bridged bicyclic lactams. J Am Chem Soc. 2007;129:2766-7 pubmed
  47. Kossakowski J, Wojciechowska A, Kozioł A. Synthesis of amino derivatives of 10-(diphenylmethylene)-4-azatricyclo[,6)]dec-8-ene-3,5-dione as potential psychotropic and/or anti HIV agents. Acta Pol Pharm. 2006;63:261-4 pubmed
    ..These compounds are expected to have antipsychotic and/or anti HIV activity. Molecular structure of III was confirmed by an X-ray structure analysis. The cytotoxicity and anti HIV activity of derivatives I-IV were determined. ..
  48. Kakehi A, Ito S, Suga H, Sakurai S, Kobayashi T. Preparation of new nitrogen-bridged heterocycles. 51. Syntheses and structures of compounds having two indolizine nuclei in a molecule. Chem Pharm Bull (Tokyo). 2001;49:1401-5 pubmed