A Diversity-Oriented Synthesis of Bicyclic cis-Dihydroarenediols, cis-4-Hydroxyscytalones, and Bicyclic Conduritol Analogues

A common-intermediate-based enantioselective strategy has been developed aiming at bicyclic arene cis-dihydrodiols, cis-4-hydroxyscytalones, and bicyclic mimics of conduritol. Key features of this protocol include Barrett’s asymmetric hydroxyallylation, ring-closing metathesis (RCM), and completely...

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Bibliographic Details
Published in:Organic letters 2010-06, Vol.12 (11), p.2472-2475
Main Authors: Mukherjee, Parag, Roy, Soumya J. Singha, Sarkar, Tarun K.
Format: Article
Language:English
Subjects:
Alcohols - chemical synthesis
Alcohols - chemistry
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Cyclization
Cycloparaffins - chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism
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Summary:A common-intermediate-based enantioselective strategy has been developed aiming at bicyclic arene cis-dihydrodiols, cis-4-hydroxyscytalones, and bicyclic mimics of conduritol. Key features of this protocol include Barrett’s asymmetric hydroxyallylation, ring-closing metathesis (RCM), and completely regioselective Wacker oxidation of internal cyclic olefins.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol100557f