受生物启发的 Gymnothelignan N 的全合成

Bioinspired total synthesis of gymnothelignan N.

机构信息

State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University , Lanzhou 730000, People's Republic of China.

出版信息

Org Lett. 2014 Sep 5;16(17):4440-3. doi: 10.1021/ol501960j. Epub 2014 Aug 8.

DOI:10.1021/ol501960j

PMID:25103476

Abstract

Bioinspired total synthesis of gymnothelignan N was accomplished in 13 steps and 6.7% overall yield. The synthesis features a syn Evans aldol reaction, an intramolecular hydrogenative dehydration reaction, and a phenol oxidative dearomatization/Friedel-Crafts reaction, which provides a new plausible biosynthetic pathway for the gymnothelignans and other symbiotic members. Meanwhile, another tetrahydrofuran-type lignan beilschmin A was also synthesized.

摘要

受生物启发，我们通过 13 步反应以 6.7%的总产率实现了 gymnothelignan N 的全合成。该合成方法的关键步骤包括：顺式 Evans 羟醛缩合反应、分子内氢解脱水反应和酚类氧化去芳构化/Friedel-Crafts 反应，为 gymnothelignans 和其他共生成员提供了新的可能生物合成途径。同时，我们还合成了另一种四氢呋喃型木脂素 beilschmin A。