Jump to main content
Jump to site search

Issue 11, 2006
Previous Article Next Article

Synthesis of the bis-spiroacetal moiety of the shellfish toxins spirolides B and D using an iterative oxidative radical cyclization strategy

Author affiliations

Abstract

The enantioselective synthesis of the bis-spiroacetal fragment of the shellfish toxins, spirolides B 1 and D 2, is reported. The carbon framework was constructed via a Barbier reaction of dihydropyran 10 with aldehyde 11, followed by two oxidative radical cyclizations to construct the bis-spiroacetal ring system. A silyl-modified Prins cyclization and enantioselective crotylation successfully installed the stereocenters in the cyclization precursor 21. The initial unsaturated bis-spiroacetals 9a–d underwent equilibration during epoxidation to trans-epoxide 24 that was converted to tertiary alcohol 7.

Graphical abstract: Synthesis of the bis-spiroacetal moiety of the shellfish toxins spirolides B and D using an iterative oxidative radical cyclization strategy

Back to tab navigation

Supplementary files

Publication details

The article was received on 27 Mar 2006, accepted on 12 Apr 2006 and first published on 02 May 2006


Article type: Paper
DOI: 10.1039/B604334H
Citation: Org. Biomol. Chem., 2006,4, 2184-2192
  •   Request permissions

    Synthesis of the bis-spiroacetal moiety of the shellfish toxins spirolides B and D using an iterative oxidative radical cyclization strategy

    K. Meilert and M. A. Brimble, Org. Biomol. Chem., 2006, 4, 2184
    DOI: 10.1039/B604334H

Search articles by author

Spotlight

Advertisements