Total Synthesis and Determination of the Absolute Configuration of Naturally Occurring Mangromicin A, with Potent Antitrypanosomal Activity

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• 作者：Hirokazu Takada ; Takeshi Yamada ; Tomoyasu Hirose ; Takuma Ishihara ; Takuji Nakashima ; Yo̅ko Takahashi ; Satoshi O̅mura ; Toshiaki Sunazuka
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：19
• 期：1
• 页码：230-233
• 全文大小：393K
• ISSN：1523-7052

文摘

An enantioselective total synthesis of (+)-mangromicin A has been accomplished. The tetrahydrofuran ring of mangromicin A, possessing a tetrasubstituted carbon center, was constructed by Mukaiyama-type vinylogous alkylation via a cyclic oxocarbenium intermediate derived from a γ-hydroxy ketone with ideal stereoselectivity, and the 4-hydroxydihydropyrone scaffold was generated via Dieckmann cyclization at a late stage of the total synthesis. The reliable asymmetric synthesis of (+)-mangromicin A has revealed the absolute configuration of naturally occurring mangromicin A.