（±）-罗斯因酮 B 的快速仿生全合成。

Rapid biomimetic total synthesis of (±)-rossinone B.

机构信息

Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Peking University, Beijing 100871, China.

出版信息

Org Lett. 2010 Dec 3;12(23):5554-7. doi: 10.1021/ol102438r. Epub 2010 Nov 9.

DOI:10.1021/ol102438r

PMID:21062011

Abstract

A biomimetic total synthesis of (±)-rossinone B has been achieved through a highly efficient strategy featuring a series of rationally designed reactions, including a one-pot allylic rearrangement/oxidation reaction to generate the vinyl quinone 27, an intramolecular vinyl quinone Diels-Alder reaction to construct the linear 6-6-5 tricyclic core of 28, and a double conjugate addition/β-elimination cascade to complete the total synthesis of 1.

摘要

通过一种高效的策略，实现了（±）-罗辛酮 B 的仿生全合成，该策略具有一系列合理设计的反应，包括一锅法烯丙基重排/氧化反应生成乙烯基醌 27、分子内乙烯基醌 Diels-Alder 反应构建线性 6-6-5 三环核心 28，以及双共轭加成/β-消除级联反应完成 1 的全合成。