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

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posted on 15.10.2008, 00:00 by Shyam Krishnan, Jeffrey T. Bagdanoff, David C. Ebner, Yeeman K. Ramtohul, Uttam K. Tambar, Brian M. Stoltz
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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