The Total Synthesis of Coleophomones B, C, and D

K. C. Nicolaou,* Tamsyn Montagnon,† Georgios Vassilikogiannakis,† and Casey J. N. Mathison
Contribution from the Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, and Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093
J. Am. Chem. Soc., 2005, 127 (24), pp 8872–8888
DOI: 10.1021/ja0509984
Publication Date (Web): May 27, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Current address:  Department of Chemistry, University of Crete, L. Knossou 300, 71409 Heraklion, Crete, Greece.

, kcn@scripps.edu

Abstract

Abstract Image

Members of the coleophomone family of natural products all possess several intriguing and challenging architectural features, as well as exhibit unusual biological activity. They, therefore, constitute attractive targets for synthesis. In this Article, we describe the total synthesis of coleophomones B (2), C (3), and D (4). The highly strained and congested 11-membered macrocycle of coleophomones B (2) and C (3) was constructed using an impressive olefin metathesis reaction. Furthermore, both of the requisite geometric isomers of the Δ16,17 within the macrocycle could be accessed from a common precursor, facilitating a divergence that lent the coleophomone B (2)/C (3) synthesis an unusually high degree of efficiency. The synthesis of coleophomone D (4) confirmed that it exists as a dynamic mixture of isomeric forms with a different aromatic substitution pattern from the other family members.

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History

  • Published In Issue June 22, 2005
  • Received February 16, 2005

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