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J Org Chem ; 72(16): 6127-34, 2007 Aug 03.
Article in English | MEDLINE | ID: mdl-17628106

ABSTRACT

The first total synthesis of (+)- and (-)-pericosine A has been achieved, enabling the revision and determination of the absolute configuration of this antitumor natural product as methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate. Every step of this total synthesis proceeded well with excellent stereoselectivity. Structures of the intermediates in crucial steps were confirmed by detailed 2D NMR analysis.


Subject(s)
Antineoplastic Agents/chemical synthesis , Carboxylic Acids/chemical synthesis , Chemistry, Organic/methods , Chemistry, Pharmaceutical/methods , Shikimic Acid/analogs & derivatives , Antineoplastic Agents/chemistry , Carboxylic Acids/chemistry , Drug Design , Magnetic Resonance Spectroscopy , Models, Chemical , Molecular Conformation , Molecular Structure , Shikimic Acid/chemical synthesis , Stereoisomerism
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