Synthesis of (+)-(S)-streptenol A and biomimetic synthesis of (2R,4S)- and(2S,4S)-2-(pent-3-enyl)piperidin-4-ol

Authors
Dollt, H Hammann, P Blechert, S
Citation
H. Dollt et al., Synthesis of (+)-(S)-streptenol A and biomimetic synthesis of (2R,4S)- and(2S,4S)-2-(pent-3-enyl)piperidin-4-ol, HELV CHIM A, 82(7), 1999, pp. 1111-1121
Citations number
19
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
HELVETICA CHIMICA ACTA
ISSN journal
0018019X → ACNP
Volume
82
Issue
7
Year of publication
1999
Pages
1111 - 1121
Database
ISI
SICI code
0018-019X(1999)82:7<1111:SO(AAB>2.0.ZU;2-B
Abstract
(+)-(S)-Streptenol A is synthesized by coupling a 1,3-dithiane with an opti cally pure epoxide. The absolute configuration of (+)-(S)-streptenol A is t hereby correlated with that of (S)-malic acid. Stereoselective reduction of an oxime that could easily be prepared from streptenol A gave the (3S,5R)- and (3S,5S)-aminostreptenols, and after cyclization, configurationally pur e 2,4-functionalized piperidine alkaloids.