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

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 h...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 129; no. 14; pp. 4150 - 4151
Main Authors Skepper, Colin K, MacMillan, John B, Zhou, Guang-Xiong, Masuno, Makoto N, Molinski, Tadeusz F
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.04.2007
Amer Chemical Soc
Subjects
Animals
Chemistry
Chemistry, Multidisciplinary
Circular Dichroism
Cyclopropanes - chemistry
Macrolides - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Physical Sciences
Porifera - chemistry
Science & Technology
PHORBOXAZOLES
RELATIVE CONFIGURATION
ABSOLUTE-CONFIGURATION
CALLIPELTOSIDE
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Summary: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.
Bibliography:ark:/67375/TPS-FLCF4RJL-7
istex:76AA204A44275390BE992B2601CBE8210DD6F3EA
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NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0703978