CaltechAUTHORS
Published October 28, 2014 | Version Supplemental Material + Published
Journal Article Open

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

Creators

  • 1. ROR icon California Institute of Technology

Abstract

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.

Additional Information

© 2014, Liu et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), 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: (http://www.beilstein-journals.org/bjoc). 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.

Attached Files

Published - 1860-5397-10-261.pdf

Supplemental Material - Beilstein_J_Org_Chem-10-2501-s001.pdf

Files

1860-5397-10-261.pdf

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Additional details

Identifiers

PMCID
PMC4222294
Eprint ID
52797
Resolver ID
CaltechAUTHORS:20141215-084337170

Funding

NIH
R01GM080269
Amgen
Gordon and Betty Moore Foundation
Caltech
Caltech Minorities Undergraduate Research Fellowship (MURF)
PREM program
Eli Lilly
Resnick Sustainability Institute
Swiss National Science Foundation (SNSF)

Dates

Created
2014-12-15
Created from EPrint's datestamp field
Updated
2021-11-10
Created from EPrint's last_modified field

Caltech Custom Metadata

Caltech groups
Resnick Sustainability Institute