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Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

Liu, Yiyang and Liniger, Marc and McFadden, Ryan M. and Roizen, Jennifer L. and Malette, Jacquie and Reeves, Corey M. and Behenna, Douglas C. and Seto, Masaki and Kim, Jimin and Mohr, Justin T. and Virgil, Scott C. and Stoltz, Brian M. (2014) Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation. Beilstein Journal of Organic Chemistry, 10 . pp. 2501-2512. ISSN 1860-5397. PMCID PMC4222294. doi:10.3762/bjoc.10.261.

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Pd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of “classic” natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.

Item Type:Article
Related URLs:
URLURL TypeDescription CentralArticle
Roizen, Jennifer L.0000-0002-6053-5512
Mohr, Justin T.0000-0002-7005-3322
Virgil, Scott C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2014, Liu et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: ( Received: 11 August 2014. Accepted: 09 October 2014. Published: 28 October 2014. Associate Editor: S. Bräse. We are grateful to NIH (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, and Caltech for funding. We also thank the Caltech Minorities Undergraduate Research Fellowship program, PREM program, Eli Lilly, the Resnick Sustainability Institute at Caltech (fellowship for Y. L.), and the Swiss National Science Foundation (SNSF, fellowship for M. L.). Dr. Michael L. Krout and Dr. David E. White are acknowledged for preliminary experimental work related to their results. Dr. Michael Takase (Caltech) and Larry Henling (Caltech) are gratefully acknowledged for X-ray crystallographic structural determination.
Group:Resnick Sustainability Institute
Funding AgencyGrant Number
Gordon and Betty Moore FoundationUNSPECIFIED
Caltech Minorities Undergraduate Research Fellowship (MURF)UNSPECIFIED
Resnick Sustainability InstituteUNSPECIFIED
Swiss National Science Foundation (SNSF)UNSPECIFIED
Subject Keywords:enantioselective alkylation, natural products, palladium
PubMed Central ID:PMC4222294
Record Number:CaltechAUTHORS:20141215-084337170
Persistent URL:
Official Citation:Liu Y, Liniger M, McFadden RM, et al. Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation. Bräse S, ed. Beilstein Journal of Organic Chemistry 2014;10:2501-2512. doi:10.3762/bjoc.10.261.
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:52797
Deposited By: Ruth Sustaita
Deposited On:15 Dec 2014 17:08
Last Modified:10 Nov 2021 19:43

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