Synthesis of the C10-C22 bis-spiroacetal domain of spirolides B and D via iterative oxidative radical cyclization

Daniel P Furkert; Margaret A Brimble

doi:10.1021/ol026605c

Synthesis of the C10-C22 bis-spiroacetal domain of spirolides B and D via iterative oxidative radical cyclization

Org Lett. 2002 Oct 17;4(21):3655-8. doi: 10.1021/ol026605c.

Authors

Daniel P Furkert¹, Margaret A Brimble

Affiliation

¹ Department of Chemistry, University of Auckland, 23 Symonds St., Auckland, New Zealand.

PMID: 12375911
DOI: 10.1021/ol026605c

Abstract

[reaction: see text] A synthetic approach to the novel bis-spiroacetal moiety of spirolides B and D is reported. The strategy hinges upon successive formation of the spirocenters at C15 and C18 by radical oxidative cyclization, followed by base-induced rearrangement of a C19-20 alpha-epoxide to introduce the C19 hydroxyl group.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetals / chemical synthesis
Acetals / chemistry*
Biological Factors / chemical synthesis
Biological Factors / chemistry*
Free Radicals
Molecular Structure
Oxidation-Reduction
Spiro Compounds / chemical synthesis
Spiro Compounds / chemistry*

Substances

Acetals
Biological Factors
Free Radicals
Spiro Compounds
spirolide B
spirolide D