ChemInform Abstract: Asymmetric Synthesis of (+)- and (-)-Streptenol A.

✍ Scribed by Dieter Enders; Thomas Hundertmark

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199930248

✦ Synopsis

Asymmetric Synthesis of (+)-and (-)-Streptenol A. -The asymmetric synthesis of (+)-streptenol (IX) is achieved in ten steps, involving the previously developed α-alkylation of RAMP hydrazone (I) followed by removal of the hydrazone moiety to furnish the key intermediate aldehyde (VI), and introduction of the pentenyl side chain by Grignard reaction as key steps. (+)-Streptenol is obtained in 23% overall yield from RAMP hydrazone. Analogously, (-)-streptenol [ent-(IX)] is accessible from SAMP hydrazone [ent-(I)] in 18% overall yield. -(ENDERS, DIETER; HUNDERTMARK, THOMAS;