Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

2015

Journal or Book Title

Organic Letters

Volume

17

Issue

15

First Page

3718

Last Page

3721

DOI

10.1021/acs.orglett.5b01702

Abstract

The breitfussins are halogenated natural products whose structures were determined with the assistance of atomic-force microscopy. The site selectivity of N-bromosuccinimide-mediated bromination of a model breitfussin core was found to be strongly dependent on solvent selection; use of acetone led to oxazole bromination, and use of a pyridine-containing mixture led to pyrrole bromination. This tunable site-selective bromination was used in a protecting-group-free synthesis of breitfussin B that proceeded in 9.2% yield over 12 reactions and five chromatographic separations. A bromooxazole analogue of breitfussin A was also prepared by late-stage bromination but isomerized on silica gel to form breitfussin B. This isomerization appeared to proceed through a unimolecular pathway.

Comments

Reprinted (adapted) with permission from Org. Lett., 2015, 17 (15), pp 3718–3721. Copyright 2015 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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