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Pure Appl. Chem., 1992, Vol. 64, No. 12, pp. 1831-1847

http://dx.doi.org/10.1351/pac199264121831

Transannular Diels-Alder reaction on macrocycles. A general strategy for the synthesis of polycyclic compounds

P. Deslongchamps

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  • Fujii Tomohiro, Nakada Masahisa: Stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade. Tetrahedron Letters 2014, 55, 1597. <http://dx.doi.org/10.1016/j.tetlet.2014.01.071>
  • Iafe Robert G., Kuo Jonathan L., Hochstatter Dustin G., Saga Tomomi, Turner Jonathan W., Merlic Craig A.: Increasing the Efficiency of the Transannular Diels–Alder Strategy via Palladium(II)-Catalyzed Macrocyclizations. Org. Lett. 2013, 15, 582. <http://dx.doi.org/10.1021/ol303394t>
  • Prathyusha V., Priyakumar U. Deva: Role of conformational properties on the transannular Diels–Alder reactivity of macrocyclic trienes with varying linker lengths. RSC Adv. 2013, 3, 15892. <http://dx.doi.org/10.1039/c3ra42045k>
  • Prathyusha V., Ramakrishna S., Priyakumar U. Deva: Transannular Diels–Alder Reactivities of 14-Membered Macrocylic Trienes and Their Relationship with the Conformational Preferences of the Reactants: A Combined Quantum Chemical and Molecular Dynamics Study. J. Org. Chem. 2012, 77, 5371. <http://dx.doi.org/10.1021/jo300812q>
  • Xue Haoran, Gopal Peddabuddi, Yang Jiong: Stereochemical Study of a Transannular Michael Reaction Cascade. J. Org. Chem. 2012, 77, 8933. <http://dx.doi.org/10.1021/jo301287z>
  • Iafe Robert G., Chan Daniel G., Kuo Jonathan L., Boon Byron A., Faizi Darius J., Saga Tomomi, Turner Jonathan W., Merlic Craig A.: Cyclization Strategies to Polyenes Using Pd(II)-Catalyzed Couplings of Pinacol Vinylboronates. Org. Lett. 2012, 14, 4282. <http://dx.doi.org/10.1021/ol3020623>
  • Marsault Eric, Peterson Mark L.: Macrocycles Are Great Cycles: Applications, Opportunities, and Challenges of Synthetic Macrocycles in Drug Discovery. J Med Chem 2011, 54, 1961. <http://dx.doi.org/10.1021/jm1012374>
  • DESLONGCHAMPS P.: ChemInform Abstract: Transannular Diels-Alder Reaction on Macrocycles. A General Strategy for the Synthesis of Polycyclic Compounds. ChemInform 2010, 24, no. <http://dx.doi.org/10.1002/chin.199311325>
  • Sparling Brian A., Simpson Graham L., Jamison Timothy F.: Strategic use of nickel(0)-catalyzed enyne–epoxide reductive coupling toward the synthesis of (−)-cyatha-3,12-diene. Tetrahedron 2009, 65, 3270. <http://dx.doi.org/10.1016/j.tet.2008.11.086>
  • Pattenden Gerald, Stoker Davey A., Thomson Nicholas M.: Cascade radical-mediated cyclisations with conjugated ynone electrophores. An approach to the synthesis of steroids and other novel ring-fused polycyclic carbocycles. Org Biomol Chem 2007, 5, 1776. <http://dx.doi.org/10.1039/b703373g>
  • Balskus E. P., Jacobsen E. N.: Asymmetric Catalysis of the Transannular Diels-Alder Reaction. Sci 2007, 317, 1736. <http://dx.doi.org/10.1126/science.1146939>
  • Dineen Thomas A., Roush William R.: Total Synthesis of Cochleamycin A. Org Lett 2004, 6, 2043. <http://dx.doi.org/10.1021/ol049331x>
  • Chantigny Yves A, Dory Yves L, Toró András, Deslongchamps Pierre: Use of the transannular Diels–Alder (TADA) reaction to probe biological receptors: Rational design and synthesis of tricyclic TADA adducts capable of rigidly holding pharmacophore parts. Can J Chem 2002, 80, 875. <http://dx.doi.org/10.1139/v02-064>
  • Marsault Eric, Toró András, Nowak Pawel, Deslongchamps Pierre: The transannular Diels–Alder strategy: applications to total synthesis. Tetrahedron 2001, 57, 4243. <http://dx.doi.org/10.1016/S0040-4020(01)00121-1>
  • Fortin Daniel, Gaudette Frédéric, Marsault Eric, Deslongchamps Pierre: Total synthesis of 3-azasteroids via the transannular Diels–Alder strategy. Tetrahedron 2001, 57, 4167. <http://dx.doi.org/10.1016/S0040-4020(01)00290-3>
  • White James D., Blakemore Paul R., Korf Eric A., Yokochi Alexandre F. T.: Transannular Nitrone Cycloaddition. A Stereocontrolled Entry to the Spirocyclic Core of Pinnaic Acid. Org Lett 2001, 3, 413. <http://dx.doi.org/10.1021/ol000361j>
  • Appendino Giovanni, Tron Gian Cesare, Jarevång Tomas, Sterner Olov: Unnatural Natural Products from the Transannular Cyclization of Lathyrane Diterpenes. Org Lett 2001, 3, 1609. <http://dx.doi.org/10.1021/ol0155541>
  • Lavoie Rico, Ouellet Stéphane G, Dallaire Carol, Dory Yves L, Toró András, Deslongchamps Pierre: Transannular Diels–Alder Studies of 14-Membered cis–trans–trans Macrocyclic Trienes Having Allylic Ether or Enone Dienophile. Tetrahedron 2000, 56, 5509. <http://dx.doi.org/10.1016/S0040-4020(00)00455-5>
  • Marsault Eric, Deslongchamps Pierre: Increasing the Efficiency of the Transannular Diels−Alder Strategy via Stille Macrocyclizations. Org Lett 2000, 2, 3317. <http://dx.doi.org/10.1021/ol000209h>
  • Toró András, L'Heureu Alexandre, Deslongchamps Pierre: Transannular Diels−Alder Studies on the Asymmetric Total Synthesis of Chatancin:  The Pyranophane Approach. Org Lett 2000, 2, 2737. <http://dx.doi.org/10.1021/ol006220z>
  • Phoenix Serge, Bourque Elyse, Deslongchamps Pierre: Progress toward the Total Synthesis of Cassaine via the Transannular Diels−Alder Strategy. Org Lett 2000, 2, 4149. <http://dx.doi.org/10.1021/ol006670r>
  • Frank Scott A, Works Andrea B, Roush William R: Studies on the synthesis of the decahydro-as-indacene ring system of (-)-spinosyn A via transannular Diels-Alder reactions of substituted (E,E,E)-cyclododeca-1,6,8-trienes. Can J Chem 2000, 78, 757. <http://dx.doi.org/10.1139/v00-045>
  • Toró András, Lemelin Charles-André, Préville Patrice, Bélanger Guillaume, Deslongchamps Pierre: Transannular Diels-Alder studies on the asymmetric synthesis of (+)-maritimol. Tetrahedron 1999, 55, 4655. <http://dx.doi.org/10.1016/S0040-4020(99)00128-3>
  • Lavoie Rico, Toró András, Deslongchamps Pierre: Synthesis of chiral trans-syn-cis and trans-anti-trans [6.6.6] tricycles by transannular Diels-Alder reaction. Tetrahedron 1999, 55, 13037. <http://dx.doi.org/10.1016/S0040-4020(99)00796-6>
  • Toró András, Wang Yuan, Deslongchamps Pierre: Transannular Diels-Alder model studies on the total synthesis of chatancin. The furanophane approach. Part 1: Assembly of the acyclic substrates. Tetrahetron Lett 1999, 40, 2765. <http://dx.doi.org/10.1016/S0040-4039(99)00323-8>
  • Toró András, Wang Yuan, Drouin Marc, Deslongchamps Pierre: Transannular Diels-Alder model studies on the total synthesis of chatancin. The furanophane approach. Part 2 [1]: Macrocyclization and Diels-Alder reaction. Tetrahetron Lett 1999, 40, 2769. <http://dx.doi.org/10.1016/S0040-4039(99)00324-X>
  • Toró AndrÁS, Deslongchamps Pierre: Facile Synthesis of Methyl 2-Formyl-5-hydroxymethyl-3-furancarboxylate. Synth Common 1999, 29, 2317. <http://dx.doi.org/10.1080/00397919908086234>
  • Couturier Michel, Dory Yves L, Rouillard François, Deslongchamps Pierre: Studies directed towards the total synthesis of aldosterone and naturally occurring analogues. A unified approach using the transannular Diels-Alder reaction. Tetrahedron 1998, 54, 1529. <http://dx.doi.org/10.1016/S0040-4020(97)10393-3>
  • Jankowski Paweł, Marczak Stanisław, Wicha Jerzy: Methods for the construction of trans-hydrindane rings and their origins in steroid chemistry. Vitamin D total synthesis. Tetrahedron 1998, 54, 12071. <http://dx.doi.org/10.1016/S0040-4020(98)00570-5>
  • Couturier Michel, Dory Yves L, Fortin Daniel, Rouillard Alain, Deslongchamps Pierre: Ab initio and semiempirical corroboration of the observed stereoselectivity in the transannular Diels-Alder reaction leading to steroids. Tetrahedron 1998, 54, 10089. <http://dx.doi.org/10.1016/S0040-4020(98)00600-0>
  • Dory Yves L., Hall Dennis G., Deslongchamps Pierre: On the mechanism of the Diels-Alder reaction of enal dienophiles. Competitive reactivity and ab initio calculations using a transannular probe. Tetrahedron 1998, 54, 12279. <http://dx.doi.org/10.1016/S0040-4020(98)00764-9>