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

Krishnan, Shyam and Bagdanoff, Jeffrey T. and Ebner, David C. and Ramtohul, Yeeman K. and Tambar, Uttam K. and Stoltz, Brian M. (2008) Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: Applications to the total synthesis of alkaloids. Journal of the American Chemical Society, 130 (41). pp. 13745-13754. ISSN 0002-7863. PMCID PMC2574996 . https://resolver.caltech.edu/CaltechAUTHORS:KRIjacs08

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja804738bDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja804738bPublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2574996/PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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
Funders:
Funding AgencyGrant Number
NIHR01GM65961-01
California Tobacco-Related Disease Research ProgramUNSPECIFIED
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
NSFUNSPECIFIED
CaltechUNSPECIFIED
GlaxoSmithKlineUNSPECIFIED
AstraZenecaUNSPECIFIED
Boehringer IngelheimUNSPECIFIED
Johnson and JohnsonUNSPECIFIED
PfizerUNSPECIFIED
MerckUNSPECIFIED
AmgenUNSPECIFIED
AbbottUNSPECIFIED
Research CorporationUNSPECIFIED
RocheUNSPECIFIED
Subject Keywords:Amino-acid derivatives; asymmetric-synthesis; kinetic resolution; lobelia alkaloids; Molecular-oxygen; tert-butanesulfinamide; coupling reactions; C-H; insertion; cyclization
Issue or Number:41
PubMed Central ID:PMC2574996
Record Number:CaltechAUTHORS:KRIjacs08
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:KRIjacs08
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:13587
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:12 May 2009 19:29
Last Modified:03 Oct 2019 00:40

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