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Article
Synthesis of Breitfussin B by Late-Stage Bromination
Organic Letters
  • Akbar H. Khan, Iowa State University
  • Jason Chen, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
1-1-2015
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
Citation Information
Akbar H. Khan and Jason Chen. "Synthesis of Breitfussin B by Late-Stage Bromination" Organic Letters Vol. 17 Iss. 15 (2015) p. 3718 - 3721
Available at: http://works.bepress.com/jason-shih-hao-chen/1/