Total synthesis of (±)-bruguierol A via an intramolecular [3+2] cycloaddition of cyclopropane 1, 1-diester Academic Article uri icon

Overview

MeSH Major

  • Hydrocarbons, Iodinated

abstract

  • Total synthesis of natural product (±)-bruguierol A was accomplished in 10-steps and with an overall 16.8% yield. The embedded unique 8-oxabicyclo[3.2.1]octane core skeleton in this natural product was constructed via a novel Sc(OTf)3-catalyzed intramolecular [3+2] cycloaddition of cyclopropane which was developed recently in this laboratory. This general synthetic strategy can be potentially applied to the synthesis of a broad range of structurally related natural products. © 2010 Elsevier Ltd. All rights reserved.

publication date

  • July 24, 2010

Research

keywords

  • Academic Article

Identity

Digital Object Identifier (DOI)

  • 10.1016/j.tet.2010.05.057

Additional Document Info

start page

  • 5671

end page

  • 5674

volume

  • 66

number

  • 30