Synthetic studies of the spirocyclic cyclohexene part of versipelostatin, a novel GRP78/Bip molecular chaperone downregulator

Shu Sasaki, Suguru Samejima, Tomoki Uruga, Kai Anzai, Natsumi Nishi, Eriko Kawakita, Ken Ichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The spirocyclic part consisting of an -acylated tetronic acid and a multisubstituted cyclohexene embedded in versipelostatin, a novel GRP78/Bip molecular chaperone downregulator, has been synthesized in enantiomerically pure form. The asymmetric synthesis of the targeted spiro4.5-1-oxa-7-decen-2,4-dione derivative was characterized by (1) stereoselective allylation at the -carbon of methylmalonate diester, in which one carboxylic acid was esterified with a D-glucose-derived chiral template, (2) construction of the tetrasubstituted cyclohexenone substructure by high-yielding ring-closing metathesis and (3) stereoselective construction of the spirocyclic tetronic acid part starting from the cyclohexenone obtained as the ring-closing metathesis product.

Original languageEnglish
Pages (from-to)147-154
Number of pages8
JournalJournal of Antibiotics
Volume66
Issue number3
DOIs
Publication statusPublished - 2013 Mar 1

Keywords

  • a-acyltetronic acid
  • asymmetric quaternary carbon
  • ring-closing metathesis
  • spirocyclic cyclohexene
  • versipelostatin

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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