Pd-Catalyzed Enantioselective Aerobic Oxidation of Secondary Alcohols: Applications to the Total Synthesis of Alkaloids
- 18 September 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (41) , 13745-13754
- https://doi.org/10.1021/ja804738b
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.Keywords
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