The Dolastatins. 19. Synthesis of Dolaisoleuine

George Pettit, Sheo Bux Singh, Jayaram K. Srirangam, Fiona Hogan-Pierson, Michael D. Williams

Research output: Contribution to journalArticle

25 Scopus citations

Abstract

The synthesis of dolaisoleuine as its ieri-butyl ester (Dil-OBut), a β-methoxy-γ-amino acid component of dolastatin 10, has been achieved employing as key step an aldol condensation between. N-(benzyloxycarbonyl)-N-methyl-(S,S)-isoleucinaland ieri-butyl acetate followed by O-methylation. The overall six-step reaction sequence to Dil proved to be convenient for routine preparation of this new amino acid and its stereochemical assignment as (3R,4S,5S)-N,O-dimethylisostatine.

Original languageEnglish (US)
Pages (from-to)1796-1800
Number of pages5
JournalJournal of Organic Chemistry
Volume59
Issue number7
DOIs
StatePublished - Apr 1 1994

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'The Dolastatins. 19. Synthesis of Dolaisoleuine'. Together they form a unique fingerprint.

  • Cite this

    Pettit, G., Singh, S. B., Srirangam, J. K., Hogan-Pierson, F., & Williams, M. D. (1994). The Dolastatins. 19. Synthesis of Dolaisoleuine. Journal of Organic Chemistry, 59(7), 1796-1800. https://doi.org/10.1021/jo00086a034