Document Detail


Asymmetric syntheses of APTO and AETD: the beta-amino acid fragments within microsclerodermins C, D and E.
MedLine Citation:
PMID:  23379896     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Efficient asymmetric syntheses of APTO and AETD, the highly functionalised beta-amino acid fragments within microsclerodermins C, D and E, are reported. The conjugate addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide to tert-butyl (E,E)-7-(triisopropylsilyloxy)hepta-2,4-dienoate and in situ enolate oxidation with (-)-camphorsulfonyloxaziridine, diastereoselective dihydroxylation of a 2,3-syn-gamma,delta-unsaturated-alpha-hydroxy-beta-amino ester derivative under Donohoe conditions, and a Julia-Kocieński olefination were used as the key steps.
Authors:
Stephen G Davies; Ai Matsuno Fletcher; Emma M Foster; James A Lee; Paul M Roberts; James E Thomson
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-2-4
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2013 Feb 
Date Detail:
Created Date:  2013-2-5     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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