Synthesis of Chromones from 1,1-Diacylcyclopropanes: Toward the Synthesis of Bromophycoic Acid E

Robert J Smith; Duong Nhu; Mitchell R Clark; Sinan Gai; Nigel T Lucas; Bill C Hawkins

doi:10.1021/acs.joc.7b00648

Synthesis of Chromones from 1,1-Diacylcyclopropanes: Toward the Synthesis of Bromophycoic Acid E

J Org Chem. 2017 May 19;82(10):5317-5327. doi: 10.1021/acs.joc.7b00648. Epub 2017 May 4.

Authors

Robert J Smith¹, Duong Nhu¹, Mitchell R Clark¹, Sinan Gai¹, Nigel T Lucas¹, Bill C Hawkins¹

Affiliation

¹ Department of Chemistry, University of Otago , Dunedin, New Zealand.

PMID: 28440639
DOI: 10.1021/acs.joc.7b00648

Abstract

A tandem deprotection-cyclization reaction of 1,1-diacylcyclopropanes is described which allows rapid access to structurally diverse 2,3-disubstituted chromones in good yields, and with straightforward purification. The utility of this reaction is showcased by the construction of the potent antibacterial marine natural product bromophycoic acid E scaffold.

Publication types

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