Syntheses of strychnan- and aspidospermatan-type alkaloids. 10. An enantioselective synthesis of (-)-strychnine through the Wieland-Gumlich aldehyde

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9427-9433

  Kuehne, Martin E ^a   Xu, Feng ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; ALDEHYDE; ASPIDOSPERMINE; CARBOXYL GROUP; ESTER; STRYCHNINE; TRYPTOPHAN;

ARTICLE; CYCLIZATION; ENANTIOMER; HYDROLYSIS; OXIDATION; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032509490     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9813989     Document Type: Article

References (16)

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3. Kuehne, M. E.; Xu, F. J. Org. Chem. 1997, 62, 7950.
4. (a) Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K. J. Am. Chem. Soc. 1954, 76, 4749.
5. (b) Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K. Tetrahedron 1963, 19, 247.
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13. The relative E/Z ratios are consistent with generation of intermediates having a relative propensity for eclipsed oxyanion and phosphorane substituents in a less polar solvent versus formation of a trans anti-periplanar orientation of these substituents in a more polar solvent.
14. 6
15. For syntheses of (-)-lochneridine and its C-20 epimer see the following paper (no. 11 of this series): Kuehne, M. E.; Xu, F. J. Org. Chem. 1998, 63, 9434.
16. Gree, R.; Tourbath, H.; Carrie, R. Tetrahedron Lett. 1986, 27, 4983.