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Synthetic studies of the spirocyclic cyclohexene part of versipelostatin, a novel GRP78/Bip molecular chaperone downregulator.
MedLine Citation:
PMID:  23361359     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.The Journal of Antibiotics advance online publication, 30 January 2013; doi:10.1038/ja.2012.124.
Authors:
Shu Sasaki; Suguru Samejima; Tomoki Uruga; Kai Anzai; Natsumi Nishi; Eriko Kawakita; Ken-Ichi Takao; Kin-Ichi Tadano
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-1-30
Journal Detail:
Title:  The Journal of antibiotics     Volume:  -     ISSN:  0021-8820     ISO Abbreviation:  J. Antibiot.     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2013-1-30     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0151115     Medline TA:  J Antibiot (Tokyo)     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Department of Applied Chemistry, Keio University, Yokohama, Japan.
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