Document Detail

Synthesis and Structure-Activity Relationship of Vicenistatin, a Cytotoxic 20-Membered Macrolactam Glycoside.
MedLine Citation:
PMID:  23015368     Owner:  NLM     Status:  Publisher    
We have developed two syntheses of vicenistatin and its analogues. Our first-generation strategy included the rapid and sequential assembly of the macrocyclic lactam by using an intermolecular Horner-Wadsworth-Emmons reaction between the C3-C13 fragment and the C1-C2, C14-C19 fragment, followed by an intramolecular Stille coupling reaction. The second-generation strategy utilized a ring-closing metathesis of a hexaene intermediate to generate the desired 20-membered macrolactam. This second-generation strategy made it possible to prepare synthetic analogues of vicenistatin, including the C20- and/or C23-demethyl analogues. Evaluation of the cytotoxic effect of these analogues indicated the importance of the fixed conformation of aglycon for determining the biological activity of the vicenistatins.
Hayato Fukuda; Yuko Nishiyama; Shiina Nakamura; Yutaro Ohno; Tadashi Eguchi; Yoshiharu Iwabuchi; Takeo Usui; Naoki Kanoh
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-9-27
Journal Detail:
Title:  Chemistry, an Asian journal     Volume:  -     ISSN:  1861-471X     ISO Abbreviation:  Chem Asian J     Publication Date:  2012 Sep 
Date Detail:
Created Date:  2012-9-27     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101294643     Medline TA:  Chem Asian J     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-9578 (Japan), Fax: (+81) 22-795-6847.
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