CaltechAUTHORS
Published October 15, 2008 | Version Accepted Version
Journal Article Open

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

Creators

  • 1. ROR icon California Institute of Technology

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.

Additional Information

© 2008 American Chemical Society. Received June 20, 2008. The authors thank the NIH-NIGMS (R01 GM65961-01), California TRDRP (postdoctoral fellowships to Y.K.R. and S.K., and predoctoral fellowship to J.T.B.), NDSEG (predoctoral fellowships to D.C.E. and U.K.T.), NSF (predoctoral fellowship to D.C.E.), Caltech, AstraZeneca, Boehringer Ingelheim, Johnson & Johnson, Pfizer, Merck, Amgen, Abbott, Research Corporation, Roche, and GlaxoSmithKline for generous funding

Attached Files

Accepted Version - nihms-69334.pdf

Files

nihms-69334.pdf

Files (784.2 kB)

Name Size
md5:7d560f49ce7bae081fd1b60708fe3b64
784.2 kB Preview Download

Additional details

Identifiers

PMCID
PMC2574996
Eprint ID
13587
DOI
10.1021/ja804738b
Resolver ID
CaltechAUTHORS:KRIjacs08

Related works

Describes
10.1021/ja804738b (DOI)

Funding

NIH
R01GM65961-01
California Tobacco-Related Disease Research Program
National Defense Science and Engineering Graduate (NDSEG) Fellowship
NSF
Caltech
GlaxoSmithKline
AstraZeneca
Boehringer Ingelheim
Johnson and Johnson
Pfizer
Merck
Amgen
Abbott
Research Corporation
Roche

Dates

Created
2009-05-12
Created from EPrint's datestamp field
Updated
2021-11-08
Created from EPrint's last_modified field