Total synthesis of the macrolide (+)-aspicilin by an asymmetrically catalyzed macrocyclization of an ω-Alkynal ester

Wolfgang Oppolzer, Rumen N. Radinov, Jef De Brabander

Research output: Contribution to journalArticle

64 Scopus citations

Abstract

ω-Alkynal ester 3, prepared from (S)-propylene oxide 4, yields the macrocyclic (6R)-allylic alcohol 2 (60% yield, 83% d.e.) in one operation via monohydroboration, boron/zinc-transmetalation and (-)-DAIB "catalyzed" intramolecular alkenylzinc/aldehyde addition. Introduction of the C(2)-C(3) double bond by selenoxide elimination (2 → 8), hydroxy-directed epoxidation (8 → 9), acetate assisted α-epoxide opening (10 → 12) and acidic methanolysis provides pure (+)-aspicilin (1) in 22% overall yield from 4.

Original languageEnglish (US)
Pages (from-to)2607-2610
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number15
DOIs
StatePublished - Apr 10 1995

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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