A diversity-oriented synthesis of bicyclic cis-dihydroarenediols, cis-4-hydroxyscytalones, and bicyclic conduritol analogues

Parag Mukherjee; Soumya J Singha Roy; Tarun K Sarkar

doi:10.1021/ol100557f

A diversity-oriented synthesis of bicyclic cis-dihydroarenediols, cis-4-hydroxyscytalones, and bicyclic conduritol analogues

Org Lett. 2010 Jun 4;12(11):2472-5. doi: 10.1021/ol100557f.

Authors

Parag Mukherjee¹, Soumya J Singha Roy, Tarun K Sarkar

Affiliation

¹ Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India.

PMID: 20443572
DOI: 10.1021/ol100557f

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemical synthesis*
Alcohols / chemistry
Bridged Bicyclo Compounds / chemical synthesis*
Bridged Bicyclo Compounds / chemistry
Cyclization
Cycloparaffins / chemistry*
Molecular Structure
Oxidation-Reduction
Stereoisomerism

Substances

Alcohols
Bridged Bicyclo Compounds
Cycloparaffins