Synthesis of Illisimonin a Skeleton by Intramolecular Diels-Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes

被引：2

作者：

Suzuki, Takahiro ^{[1
]}

Nagahama, Riko ^{[2
]}

Fariz, Muhammad Aiman ^{[1
]}

Yukutake, Yuki ^{[2
]}

Ikeuchi, Kazutada ^{[1
]}

Tanino, Keiji ^{[1
]}

机构：

[1] Hokkaido Univ, Dept Chem, Sapporo, Hokkaido 0600810, Japan

[2] Hokkaido Univ, Grad Sch Chem Sci & Engn, Sapporo, Hokkaido 0600810, Japan

来源：

ORGANICS | 2021年 / 2卷 / 03期

关键词：

biomimetic synthesis; Diels-Alder reaction; illicium sesquiterpene; natural product synthesis; skeletal rearrangement; NEUROTROPHIC ACTIVITY; SESQUITERPENES; (-)-JIADIFENOLIDE; ANISATIN;

D O I：

10.3390/org2030016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Illisimonin A is a new sesquiterpene isolated from Illicium simonsii, and it possesses a novel 5/5/5/5/5 pentacyclic skeleton. The tricyclic skeleton of illisimonin A, tricyclo[5.2.1.0(1,5)]decane, is presumed to be biosynthesized from allo-cedranes via a skeletal rearrangement. Herein, we report the concise synthesis of highly oxidized allo-cedranes by an intramolecular Diels-Alder reaction using ortho-benzoquinones and demonstrate the biomimetic transformation of allo-cedranes by a retro-Claisen/aldol pathway.

引用

页码：306 / 312

页数：7

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