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

研究成果: Article査読

3 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)147-154
ページ数8
ジャーナルJournal of Antibiotics
66
3
DOI
出版ステータスPublished - 2013 3 1

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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