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

Shyam Krishnan; Jeffrey T. Bagdanoff; David C. Ebner; Yeeman K. Ramtohul; Uttam K. Tambar; Brian M. Stoltz

doi:10.1021/ja804738b

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

Shyam Krishnan, Jeffrey T. Bagdanoff, David C. Ebner, Yeeman K. Ramtohul, Uttam K. Tambar, Brian M. Stoltz

Research output: Contribution to journal › Article › peer-review

140 Scopus citations

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.

Original language	English (US)
Pages (from-to)	13745-13754
Number of pages	10
Journal	Journal of the American Chemical Society
Volume	130
Issue number	41
DOIs	https://doi.org/10.1021/ja804738b
State	Published - Oct 15 2008

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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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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AU - Krishnan, Shyam

AU - Bagdanoff, Jeffrey T.

AU - Ebner, David C.

AU - Ramtohul, Yeeman K.

AU - Tambar, Uttam K.

AU - Stoltz, Brian M.

PY - 2008/10/15

Y1 - 2008/10/15

N2 - 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.

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

Abstract

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