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

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.

SUBMITTER: Krishnan S

PROVIDER: S-EPMC2574996 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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

Krishnan Shyam S Bagdanoff Jeffrey T JT Ebner David C DC Ramtohul Yeeman K YK Tambar Uttam K UK Stoltz Brian M BM

Journal of the American Chemical Society 20080918 41

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. ...[more]

PMID: 18798630

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