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 journalArticle

111 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)13745-13754
Number of pages10
JournalJournal of the American Chemical Society
Volume130
Issue number41
DOIs
StatePublished - Oct 15 2008

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Lobeline
Alkaloids
Alcohols
Oxidation
aurantioclavine
amurensinine
sedamine

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols : Applications to the total synthesis of alkaloids. / Krishnan, Shyam; Bagdanoff, Jeffrey T.; Ebner, David C.; Ramtohul, Yeeman K.; Tambar, Uttam K.; Stoltz, Brian M.

In: Journal of the American Chemical Society, Vol. 130, No. 41, 15.10.2008, p. 13745-13754.

Research output: Contribution to journalArticle

Krishnan, Shyam ; Bagdanoff, Jeffrey T. ; Ebner, David C. ; Ramtohul, Yeeman K. ; Tambar, Uttam K. ; Stoltz, Brian M. / Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols : Applications to the total synthesis of alkaloids. In: Journal of the American Chemical Society. 2008 ; Vol. 130, No. 41. pp. 13745-13754.
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