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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The NARC-Based Approach to the Enantioselective Synthesis of the Zaragozic Acids. Synthesis of a C 5-Alkoxycarbonyl-Substituted 2,8-Dioxabicyclo[3.2.1]octane.

Patrick Perlmutter and Walailak Selajarern

Australian Journal of Chemistry 53(4) 349 - 353
Published: 2000

Abstract

A direct method for the preparation of C 5-alkoxycarbonyl-substituted 2,8-dioxabicyclo[3.2.1]octanes is described. The key process involves a highly stereoselective (NARC) sequence of a nucleophilic addition followed by ring closure.

Keywords: Aldol; anti-cholesterol; bicyclic acetal; heterocycle; NARC (nucleophilic addition– ring closure); squalestatin; stereoselective; synthesis; Wacker; zaragozic acid.

https://doi.org/10.1071/CH00045

© CSIRO 2000

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