Semisynthesis of an antifungal lipopeptide echinocandin

M. Journet, D. Cai, L. M. Dimichele, D. L. Hughes, R. D. Larsen, T. R. Verhoeven, P. J. Reider

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

Compound 1 is a macrocyclic lipopeptide belonging to the echinocandin family, which has been effective in treating systemic fungal infections. In this paper, we report a unique regio-, chemo-, and stereoselective synthesis of 1 in four steps from the deacylated nucleus 3 in an impressive 83% overall yield. Highlights of this synthesis include a selective reduction of the amide to the amine and a highly stereoselective (99:1 α/β) introduction of the 2-aminoethyl hemiaminal. In addition, the synthesis of the naphthoyl side chain was accomplished in three steps in 79% overall isolated yield from commercially available 6-bromo-2-naphthol.

Original languageEnglish (US)
Pages (from-to)2411-2417
Number of pages7
JournalJournal of Organic Chemistry
Volume64
Issue number7
DOIs
StatePublished - Apr 2 1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Semisynthesis of an antifungal lipopeptide echinocandin'. Together they form a unique fingerprint.

Cite this