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; Tadeusz F. Molinski

doi:10.1021/ja0703978

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, Tadeusz F. Molinski

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	4150-4151
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	14
DOIs	https://doi.org/10.1021/ja0703978
State	Published - Apr 11 2007

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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AU - Skepper, Colin K.

AU - MacMillan, John B.

AU - Zhou, Guang Xiong

AU - Masuno, Makoto N.

AU - Molinski, Tadeusz F.

PY - 2007/4/11

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N2 - 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.

AB - 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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Chlorocyclopropane macrolides from the marine sponge Phorbas sp. assignment of the configurations of phorbasides A and B by quantitative CD

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