Formal total synthesis of enigmazole A

Andreas Meissner, Takayuki Kishi, Yuka Fujisawa, Yuto Murai, Hiroyoshi Takamura, Isao Kadota

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A stereoselective formal total synthesis of enigmazole A, a marine macrolide isolated from Cinachyrella enigmatica, is described. Lewis acid mediated intramolecular allylation of an α-acetoxy ether, prepared from alcohol and carboxylic acid fragments was carried out to construct the methylene THP ring with high stereoselectivity. The late-stage macrolactonization of the corresponding seco-acid provided a known synthetic intermediate of enigmazole A.

Original languageEnglish
Pages (from-to)4492-4495
Number of pages4
JournalTetrahedron Letters
Volume59
Issue number51
DOIs
Publication statusPublished - Dec 19 2018

Keywords

  • Allylation
  • Convergent synthesis
  • Enigmazole A
  • Macrolide
  • Reductive acetylation
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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