Enantioselective Total Synthesis of (+)-Alterbrassicicene C

Noah J Sims; Weston C Bonnet; Danielle M Lawson; John L Wood

doi:10.1021/jacs.2c12275

Enantioselective Total Synthesis of (+)-Alterbrassicicene C

J Am Chem Soc. 2023 Jan 11;145(1):37-40. doi: 10.1021/jacs.2c12275. Epub 2022 Dec 23.

Authors

Noah J Sims¹, Weston C Bonnet¹, Danielle M Lawson¹, John L Wood¹

Affiliation

¹ Department of Chemistry and Biochemistry, Baylor University, One Bear Place 97348, Waco, Texas 76798, United States.

Abstract

Herein, the first total synthesis of (+)-alterbrassicicene C (2) is described. Key features of the synthesis include an oxiranium mediated ether ring expansion, an oxa-Michael/retro-oxa-Michael cascade, and installation of a vinyl methoxy ether moiety via Stille coupling.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, N.I.H., Extramural

MeSH terms

Ethers*
Stereoisomerism

Substances

Ethers

Grants and funding

R01 GM136759/GM/NIGMS NIH HHS/United States