Asymmetric Total Synthesis of Dankasterones A and B and Periconiastone A Through Radical Cyclization.

Angewandte Chemie
Pengquan ChenZhiqiang Ma

Abstract

We describe herein the assembly of the cis-decalin framework through radical cyclization initiated by metal-catalyzed hydrogen atom transfer (MHAT), further applied it in the asymmetric synthesis of dankasterones A and B and periconiastone A. Position-selective C-H oxygenation allowed for installation of the necessary functionality. A radical rearrangement was adopted to create 13(14→8)abeo-8-ergostane skeleton. Interconversion of dankasterone B and periconiastone A was realized through biomimetic intramolecular aldol and retro-aldol reactions. The MHAT-based approach, serves as a new dissection means, is complementary to the conventional ways to establish cis-decalin framework.

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Citations

Feb 9, 2021·Journal of the American Chemical Society·Darius VrubliauskasChristopher D Vanderwal
Mar 25, 2021·Journal of the American Chemical Society·Xinghui LiJinghan Gui
May 6, 2021·Organic & Biomolecular Chemistry·Zhuo Wang, Chunngai Hui
Apr 7, 2021·Angewandte Chemie·Zhengyuan XinShuanhu Gao
Aug 28, 2021·Chemical Science·Tianze ZhangHanmin Huang
Oct 20, 2021·Angewandte Chemie·Cheng WangZhiqiang Ma

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