Dichloroketene-chiral olefin-based approach to pyrrolizidines: Highly stereocontrolled synthesis of (+)-amphorogynine A

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1741-1744

  Roche, Caroline ^a   Delair, Philippe ^a   Greene, Andrew E ^a  

^a UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOROGYNINE A; PYRROLIZINE DERIVATIVE; UNCLASSIFIED DRUG; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; OSMIUM TETRAOXIDE; PYRROLIZIDINE ALKALOID;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; DIASTEREOISOMER; EXTRACTION; PLANT; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; CHEMISTRY; CONFORMATION; CYCLIZATION; MEDICINAL PLANT; NEW CALEDONIA; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSICAL CHEMISTRY; STEREOISOMERISM;

CHEMISTRY, PHYSICAL; CYCLIZATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NEW CALEDONIA; OSMIUM TETROXIDE; PLANTS, MEDICINAL; PYRROLIZIDINE ALKALOIDS; STEREOISOMERISM;

EID: 0043231395     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034369f     Document Type: Article

References (30)

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15. Molecular modeling was performed on a SGI02 workstation running Insight II Discover 2000 (ACCELRYS, San Diego). The structure was energy minimized with the force field cvff.frc. and the minimization algorithm VA09A. The molecular dynamics study was performed at 1000 K in a vacuum (dielectric constant fixed at 1; 400 000 steps of 1 fs) and consisted of generation of 500 structures. For 3b, the conformation is lowest in energy by 1.5 kcal/mol. (The next lowest in energy would also be expected to undergo cycloaddition largely on the Cα-re face.)
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24. For a similar transformation, see: Ley, S. V.; Brown, D. S.; Clase, J. A.; Fairbanks, A. J.; Lennon, I. C.; Osborn, H. M. I.; Stokes, E. S. E.; Wadsworth, D. J. J. Chem. Soc., Perkin Trans. 1 1998, 2259-2276. See also: Martinelli, M. J.; Vaidyanathan, R.; Pawlak, J. M.; Nayyar, N. K.; Dhokte, U. P.; Doecke, C. W.; Zollars, L. M. H.; Moher, E. D.; Khau, V. V.; Kosmrlj, B. J. Am. Chem. Soc. 2002, 124, 3578-3585.
25. For a similar transformation, see: Ley, S. V.; Brown, D. S.; Clase, J. A.; Fairbanks, A. J.; Lennon, I. C.; Osborn, H. M. I.; Stokes, E. S. E.; Wadsworth, D. J. J. Chem. Soc., Perkin Trans. 1 1998, 2259-2276. See also: Martinelli, M. J.; Vaidyanathan, R.; Pawlak, J. M.; Nayyar, N. K.; Dhokte, U. P.; Doecke, C. W.; Zollars, L. M. H.; Moher, E. D.; Khau, V. V.; Kosmrlj, B. J. Am. Chem. Soc. 2002, 124, 3578-3585.
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29. 3).
30. Note added in revision: A chiral-pool approach to amphorogynine A has just appeared. See: Yoda, H.; Egawa, T.; Takabe, K. Tetrahedron Lett. 2003, 44, 1643-1646.