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A General Approach to 1‐Hydroxymethylquinolizidine and 8‐Hydroxymethylindolizidine Stereoisomers: Synthesis of (+)‐Epitashiromine and Formal Syntheses of (+)‐Epilupinine and (+)‐Tashiromine
Author(s) -
Thorat Rakesh G.,
Pansare Sunil V.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301078
Subject(s) - quinolizidine , indolizidine , chemistry , nitrone , stereoselectivity , stereochemistry , formal synthesis , substituent , enantioselective synthesis , organic chemistry , cycloaddition , alkaloid , catalysis
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.