Multigram Synthesis of Glyceollin I

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• 作者：Amarjit Luniwal ; Rahul Khupse ; Michael Reese ; Jidong Liu ; Mohammad El-Dakdouki ; Neha Malik ; Lei Fang ; Paul Erhardt
• 刊名：Organic Process Research & Development
• 出版年：2011
• 出版时间：September 16, 2011
• 年：2011
• 卷：15
• 期：5
• 页码：1149-1162
• 全文大小：1119K
• 年卷期：v.15,no.5(September 16, 2011)
• ISSN：1520-586X

文摘

Scaled-up procedures and preparation of glyceollin I in multigram quantities are described. The synthesis features construction of a cis-fused ring system in high enantiomeric excess after Sharpless asymmetric dihydroxylation of a key intermediate that is initially produced by an intramolecular Wittig reaction to afford the requisite alkene while simultaneously forming the first ring. The overall yield is 12% after 11 steps.