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- Title
Synthetic studies of the spirocyclic cyclohexene part of versipelostatin, a novel GRP78/Bip molecular chaperone downregulator.
- Authors
Sasaki, Shu; Samejima, Suguru; Uruga, Tomoki; Anzai, Kai; Nishi, Natsumi; Kawakita, Eriko; Takao, Ken-ichi; Tadano, Kin-ichi
- Abstract
The spirocyclic part consisting of an α-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 spiro[4.5]-1-oxa-7-decen-2,4-dione derivative was characterized by (1) stereoselective allylation at the α-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.
- Publication
The Journal of antibiotics, 2013, Vol 66, Issue 3, p147
- ISSN
1881-1469
- Publication type
Journal Article
- DOI
10.1038/ja.2012.124