Scalable Synthesis of Cyclocitrinol

Yu Wang; Wei Ju; Hailong Tian; Weisheng Tian; Jinghan Gui

doi:10.1021/jacs.8b06444

Scalable Synthesis of Cyclocitrinol

J Am Chem Soc. 2018 Aug 1;140(30):9413-9416. doi: 10.1021/jacs.8b06444. Epub 2018 Jul 19.

Authors

Yu Wang¹, Wei Ju¹, Hailong Tian¹, Weisheng Tian¹, Jinghan Gui¹

Affiliation

¹ CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.

PMID: 30008202
DOI: 10.1021/jacs.8b06444

Abstract

A 10-step synthesis of the C25 steroid natural product cyclocitrinol from inexpensive, commercially available pregnenolone is reported. This synthesis features a biomimetic cascade rearrangement to efficiently construct the challenging bicyclo[4.4.1] A/B ring system, which enabled a gram-scale synthesis of the bicyclo[4.4.1] enone intermediate 18 in only nine steps. This work also provides experimental support for the biosynthetic origin of cyclocitrinol.

Publication types

Research Support, Non-U.S. Gov't