Concise Synthesis of 9,11-Secosteroids Pinnigorgiols B and E

Pinnigorgiols B and E are 9,11-secosteroids with a unique tricyclic γ-diketone framework. Herein, we report the first synthesis of these natural products from inexpensive, commercially available ergosterol. This synthesis features a semipinacol rearrangement and an acyl radical cyclization/hemiketal...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2021-04, Vol.143 (13), p.4886-4890
Main Authors: Li, Xinghui, Zhang, Zeliang, Fan, Huafang, Miao, Yinlong, Tian, Hailong, Gu, Yucheng, Gui, Jinghan
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Pinnigorgiols B and E are 9,11-secosteroids with a unique tricyclic γ-diketone framework. Herein, we report the first synthesis of these natural products from inexpensive, commercially available ergosterol. This synthesis features a semipinacol rearrangement and an acyl radical cyclization/hemiketalization cascade; the latter efficiently assembled the tricyclic γ-diketone skeleton, with two rings and three contiguous stereogenic centers being formed in a single step.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c13426