Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: applications to the total synthesis of alkaloids

…, JT Bagdanoff, DC Ebner, YK Ramtohul…

Index: Krishnan, Shyam; Bagdanoff, Jeffrey T.; Ebner, David C.; Ramtohul, Yeeman K.; Tambar, Uttam K.; Stoltz, Brian M. Journal of the American Chemical Society, 2008 ,  vol. 130,  # 41  p. 13745 - 13754

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Citation Number: 106

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 ...