Chlorocyclopropane Macrolides from the Marine Sponge Phorbas sp. Assignment of the Configurations of Phorbasides A and B by Quantitative CD

Colin K. Skepper,†‡ John B. MacMillan,‡§ Guang-Xiong Zhou,‡ Makoto N. Masuno,‡ and Tadeusz F. Molinski*†‡
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093, Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616
J. Am. Chem. Soc., 2007, 129 (14), pp 4150–4151
DOI: 10.1021/ja0703978
Publication Date (Web): March 21, 2007
Copyright © 2007 American Chemical Society
†

 University of California, San Diego.

,
‡

 University of California, Davis.

,
§

 Present address:  University of Texas, Southwestern Medical Center, Dept. of Biochemistry, 5323 Harry Hines Blvd., Dallas, TX 75390.

,
*

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

, tmolinski@ucsd.edu

Abstract

Abstract Image

Two new chlorocyclopropane macrolides, phorbasides A and B, have been characterized from the sponge Phorbas sp. that previously yielded phorboxazoles A and B. We describe the assignment of the absolute configuration of the trans-chlorocyclopropane ring that exploits a CD Cotton effect arising from hyperconjugation to the ene-yne chromophore. Phorbasides and callipeltoside A share the same macrolide configurations but, unexpectedly, opposite cyclopropane configurations.

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History

  • Published In Issue April 11, 2007
  • Received January 24, 2007

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