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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