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 journalArticle

35 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 languageEnglish (US)
Pages (from-to)4150-4151
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number14
DOIs
StatePublished - Apr 11 2007

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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