An enantiocontrolled entry to the tricyclic polar segment of (+)-fusarisetin A

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• 作者：Aki Kohyama^a ; Naoki Kanoh^a ; Eunsang Kwon^b ; Yoshiharu Iwabuchi^a ; ^{y-iwabuchi@m.tohoku.ac.jp" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Fusarisetin A ; Yamamoto asymmetric epoxidation ; Epoxide ring opening ; Oxidative lactonization
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：3 February 2016
• 年：2016
• 卷：57
• 期：5
• 页码：517-519
• 全文大小：383 K

文摘

The tricyclic polar segment of fusarisetin A, designed for preparing analogues for structure–activity relationship studies of the aliphatic segment thereof, has been constructed in an enantiocontrolled manner, featuring the Yamamoto asymmetric epoxidation of a homoallylic alcohol, C3-selective ring-opening of a 3,4-epoxy alcohol, stereocontrolled merger of a γ-lactone with Garner’s counterpart, and ruthenium-catalyzed ring-closing metathesis.