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. 2008 Oct 15;130(41):13745-54.
doi: 10.1021/ja804738b. Epub 2008 Sep 18.

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

Shyam Krishnan  1 , Jeffrey T Bagdanoff, David C Ebner, Yeeman K Ramtohul, Uttam K Tambar, Brian M Stoltz
Affiliations

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

Shyam Krishnan et al. J Am Chem Soc. .

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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Figures

Scheme 1a
Scheme 1a
Scheme 1b
Scheme 1b
Figure 1
Figure 1
Alkaloids with nitrogen-bearing stereocenters.
Scheme 2
Scheme 2
Figure 2
Figure 2
The isopavine natural products.
Scheme 3
Scheme 3
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Scheme 20
See this image and copyright information in PMC

References

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