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Synthesis of (+)‐( S )‐Streptenol A and Biomimetic Synthesis of (2 R ,4 S )‐ and (2 S ,4 S )‐2‐(Pent‐3‐enyl)piperidin‐4‐ol
Author(s) -
Dollt Heribert,
Hammann Peter,
Blechert Siegfried
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19990707)82:7<1111::aid-hlca1111>3.0.co;2-l
Subject(s) - chemistry , piperidine , stereoselectivity , oxime , dithiane , stereochemistry , absolute configuration , epoxide , malic acid , organic chemistry , catalysis , citric acid
(+)‐( S )‐Streptenol A is synthesized by coupling a 1,3‐dithiane with an optically pure epoxide. The absolute configuration of (+)‐( S )‐streptenol A is thereby correlated with that of ( S )‐malic acid. Stereoselective reduction of an oxime that could easily be prepared from streptenol A gave the (3 S ,5 R )‐ and (3 S ,5 S )‐aminostreptenols, and after cyclization, configurationally pure 2,4‐functionalized piperidine alkaloids.