Enantioselective total synthesis of sacrolide A

Tomoyo Mohri, Yusuke Ogura, Ryo Towada, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

An enantioselective total synthesis of sacrolide A, an antimicrobial and cytotoxic fourteen-membered macrolactonic oxylipin isolated from an edible freshwater cyanobacterium, has been accomplished from a known carboxylic acid in 20% overall yield by a concise ten-step sequence. The key transformations include chiral oxazolidinone-based diastereoselective installation of two hydroxy-bearing stereocenters, the Horner–Wadsworth–Emmons olefination to construct the full carbon skeleton, and the Shiina macrolactonization to establish the fourteen-membered macrolide structure.

Original languageEnglish
Pages (from-to)4011-4013
Number of pages3
JournalTetrahedron Letters
Volume58
Issue number42
DOIs
Publication statusPublished - 2017 Jan 1

Keywords

  • Antimicrobial
  • Macrolide
  • Oxylipin
  • Sacrolide
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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