Gram-Scale Synthesis of (+)-Spongistatin 1: Development of An Improved, Scalable Synthesis of the F-Ring Subunit, Fragment Union, and Final Elaboration

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• 作者：Amos B. Smith ; ; Takashi Tomioka ; Christina A. Risatti ; Jeffrey B. Sperry ; Chris Sfouggatakis
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：October 2, 2008
• 年：2008
• 卷：10
• 期：19
• 页码：4359-4362
• 全文大小：179K
• 年卷期：v.10,no.19(October 2, 2008)
• ISSN：1523-7052

文摘

In a quest to develop an effective, scalable synthesis of (+)-spongistatin 1 (1), we devised a concise, third-generation scalable synthesis of (+)-7, the requisite F-ring tetrahydropyran aldehyde, employing a proline-catalyzed cross-aldol reaction. Subsequent elaboration to (+)-EF Wittig salt (+)-3, followed by union with advanced ABCD aldehyde (−)-4, macrolactonization and global deprotection permitted access to >1.0 g of totally synthetic (+)-spongistatin 1 (1).