Synthesis of the cyclic heptapeptides Axinastatin 2 and Axinastatin 3

George Pettit, Jeffrey W. Holman, Gerard M. Boland

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Practical total syntheses of axinastatins 2 2b and 3 2c were completed by employing Fmoc protection for the N-terminal, and tert-butyl ester blocking for the C-terminal, units of the amlno add and peptide intermediates. Generally, diethyl phosphorocyanidate proved effective for formation of the peptide bond, and in the one exception, asparagine, the o-nitrophenyl active ester proved to be useful. For the final cyclization reaction BOP-Cl was found especially effective.

Original languageEnglish (US)
Pages (from-to)2411-2416
Number of pages6
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number19
StatePublished - Oct 7 1996

Fingerprint

Esters
Peptides
Asparagine
Cyclization
axinastatin 3
axinastatin 2
bis(2-oxo-3-oxazolidinyl)phosphinic chloride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of the cyclic heptapeptides Axinastatin 2 and Axinastatin 3. / Pettit, George; Holman, Jeffrey W.; Boland, Gerard M.

In: Journal of the Chemical Society - Perkin Transactions 1, No. 19, 07.10.1996, p. 2411-2416.

Research output: Contribution to journalArticle

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