A cobaloxime-mediated synthesis of the ras farnesyl-protein transferase inhibitor chaetomellic acid A

Bruce Branchaud, Rachel M. Slade

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

A short and efficient synthesis of chaetomellic acid A anhydride (2) is reported utilizing a doubly chemoselective cross coupling of myristyl cobaloxime with citraconic anhydride and diphenyl disulfide as the key step. Sulfide oxidation followed by syn elimination provides 2 in 64% overall yield starting from myristyl bromide. Basic hydrolysis of 2 is known to provide chaetomellic acid A dianion (3), the biologically active form.

Original languageEnglish (US)
Pages (from-to)4071-4072
Number of pages2
JournalTetrahedron Letters
Volume35
Issue number24
DOIs
StatePublished - Jun 13 1994
Externally publishedYes

Fingerprint

ras Proteins
Transferases
Anhydrides
Sulfides
Bromides
Hydrolysis
Proteins
Oxidation
cobaloxime
chaetomellic acid A
diphenyl disulfide
citraconic anhydride

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A cobaloxime-mediated synthesis of the ras farnesyl-protein transferase inhibitor chaetomellic acid A. / Branchaud, Bruce; Slade, Rachel M.

In: Tetrahedron Letters, Vol. 35, No. 24, 13.06.1994, p. 4071-4072.

Research output: Contribution to journalArticle

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