Pd-catalyzed Enantioselective Aerobic Oxidation of Secondary Alcohols: Applications to the Total Synthesis of Alkaloids

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2008 Sep 19

PMID 18798630

Citations 13

Authors

Shyam Krishnan

Jeffrey T Bagdanoff

David C Ebner

Yeeman K Ramtohul

Uttam K Tambar

Brian M Stoltz

Affiliations

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Abstract

Enantioselective syntheses of the alkaloids (-)-aurantioclavine, (+)-amurensinine, (-)-lobeline, and (-)- and (+)-sedamine are described. The syntheses demonstrate the effectiveness of the Pd-catalyzed asymmetric oxidation of secondary alcohols in diverse contexts and the ability of this methodology to set the absolute configuration of multiple stereocenters in a single operation. The utility of an aryne C-C insertion reaction in accessing complex polycyclic frameworks is also described.

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