A divergent enantioselective synthesis of 9-J1-phytoprostane and 9-A1-phytoprostane methyl ester

Alessio Porta, Francesco Chiesa, Marco Quaroni, Marco Persico, Remigio Moratti, Giuseppe Zanoni, Giovanni Vidari

Research output: Contribution to journalArticlepeer-review

Abstract

The first syntheses of 9-J1-phytoprostane and 9-A 1-phytoprostane methyl ester were achieved enantioselectively using a divergent approach from a common intermediate sulfone 4. The divergence was accomplished using a sigmatropic rearrangement (swap protocol) to give sulfone 5 in 47% overall yield. The two upper side-chains, with a stereodefined E double bond, were installed using consolidated Julia-Lythgoe olefination reactions of sulfones 4 and 5, with the same enantiopure α-protected aldehyde 6.

Original languageEnglish
Pages (from-to)2111-2119
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number10
DOIs
Publication statusPublished - 2014

Keywords

  • Asymmetric synthesis
  • Natural products
  • Olefination
  • Phytoprostanes
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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