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- Title
A General Approach to 1-Hydroxymethylquinolizidine and 8-Hydroxymethylindolizidine Stereoisomers: Synthesis of (+)-Epitashiromine and Formal Syntheses of (+)-Epilupinine and (+)-Tashiromine.
- Authors
Thorat, Rakesh G.; Pansare, Sunil V.
- Abstract
A general strategy for the synthesis of structurally and stereochemically related indolizidine and quinolizidine alkaloids was developed. The methodology involves regio- and stereoselective 1,3-dipolar cycloadditions of simple nitrones with ephedrine-derived alkylidenemorpholinones. The intermediate isoxazolidines can be converted into either the indolizidine or the quinolizidine motif depending on the nitrone and the substituent on the dipolarophile. The approach was applied to the synthesis of (+)-epitashiromine and to the formal syntheses of (+)-epilupinine and (+)-tashiromine.
- Subjects
ALKALOID synthesis; INDOLIZIDINES synthesis; QUINOLIZIDINES synthesis; STEREOSELECTIVE reactions; REGIOSELECTIVITY (Chemistry); RING formation (Chemistry); NITRONES; ISOXAZOLIDINES
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 32, p7282
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301078