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Synthesis of Chiral Prostaglandin (Pge2) Via Stork Intermediate By Using Vinylzincates For Conjugate Addition1)

 

作者: Takashi Takahashi,   Makoto Nakazawa,   Kazuhiko Takatori,   Seijiro Nishimura,   Keiji Yamamoto,  

 

期刊: Natural Product Letters  （Taylor Available online 1993）
卷期: Volume 1, issue 4  

页码: 263-267

 

ISSN:1057-5634

 

年代: 1993

 

DOI:10.1080/10575639308050058

 

出版商: Taylor & Francis Group

 

关键词: chiral synthesis;prostaglandin;vinylzincate;conjugate addition

 

数据来源: Taylor

 

摘要:

We report here the synthesis of chiral PGE2methyl ester as a bissilyl etherviaStork intermediate, which involves the conjugate addition of lithium (E)-vinyldimethylzincate to 4-t-butyldimethylsiloxy-2-cyciopentenone followed by the formaldehyde trapping of the kinetic enolate to give eventually rise to a 2-methylenecyclopentanone derivative, the latter being subjected to the conjugate addition of another (Z)-vinylzincate.

 

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