Synthesis of acremines A, B and F and studies on the bisacremines

Nils Winter, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

The acremines are a family of meroterpenoids isolated from fungi of the genus Acremonium. Here, we present the asymmetric total synthesis of acremine F which hinges on a modestly enantioselective dihydroxylation and a subsequent kinetic resolution via a highly selective asymmetric reduction. Chemoselective oxidation of acremine F gave access to acremines A and B. The dimerization of acremine F to bisacremine E was investigated but could not be achieved, shedding light on the formation of the acremine dimers in nature.

Original languageEnglish (US)
Pages (from-to)2271-2276
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume15
DOIs
StatePublished - Sep 23 2019

Keywords

  • Meroterpenoid
  • Natural product
  • Selective oxidation
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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