Total synthesis of (-)-CP2-disorazole C1

Chad D. Hopkins, John C. Schmitz, Edward Chu, Peter Wipf

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

The total synthesis of a bis-cyclopropane analog of the antimitotic natural product (-)-disorazole C1 was accomplished in 23 steps and 1.1% overall yield. A vinyl cyclopropane cross-metathesis reaction generated a key (E)-alkene segment of the target molecule. IC50 determinations of (-)-CP2-disorazole C1 in human colon cancer cell lines indicated low nanomolar cytotoxic properties. Accordingly, this synthetic bioisostere represents the first biologically active disorazole analog not containing a conjugated diene or polyene substructure element.

Original languageEnglish (US)
Pages (from-to)4088-4091
Number of pages4
JournalOrganic Letters
Volume13
Issue number15
DOIs
StatePublished - Aug 5 2011
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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