Diastereoselective total synthesis of 8-epigrosheimin

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• 作者：Haishen Yang ; Xiaoxiao Qiao ; Fangyi Li ; Hui Ma ; Longguan Xie ; Xiaohua Xu
• 刊名：Tetrahedron Letters
• 出版年：2009
• 出版时间：11 March 2009
• 年：2009
• 卷：50
• 期：10
• 页码：1110-1112
• 全文大小：161 K

文摘

The first diastereoselective total synthesis of 8-epigrosheimin was accomplished relying entirely on substrate-controlled methods. 8-Epigrosheimin, isolated as an amoebicidal and antibiotic compound from Crepis virens, is a multi-chiral-centered guaianolide with a cis-hydroazulene and a trans-annulated γ-butyrolactone ring. Our approach featured that the γ-butyrolactone unit was formed firstly before the construction of the cycloheptane ring system. The key steps of the synthesis involved (1) a stereoselective Mukaiyama aldol addition; (2) an oxidative γ-lactonization; and (3) an intramolecular aldehyde-ene cyclization.