Synthesis of Azotomycin

George Pettit, Paul S. Nelson

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Total synthesis of the Streptomyces ambofaciens anticancer constituents (–)-azotomycin (1) from γ-OBzb N-Boc-L-Glu (3) has been accomplished in nine steps. Selective protection with N-tert-butoxycarbonyl and N-trifluoroacetyl for the amino groups and benzyl or methyl esters for carboxyl groups, combined with the mixed carbonic anhydride peptide bond forming procedure, comprised the general strategy. Synthesis of bis diazo ketone 9 from dicarboxylic acid 8a proved challenging and required development of precise experimental conditions for treating the diacid chloride intermediate with diazomethane. The (–)-azotomycin synthesis presents a useful alternative to the original fermentation-isolation route.

Original languageEnglish (US)
Pages (from-to)1282-1286
Number of pages5
JournalJournal of Organic Chemistry
Volume51
Issue number8
DOIs
StatePublished - Jan 1 1986

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of Azotomycin'. Together they form a unique fingerprint.

  • Cite this