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Catalytic enantioselective total synthesis of (+)-eucomic acid

Estipona, Benzi I. and Pritchett, Beau P. and Craig, Robert A., II and Stoltz, Brian M. (2016) Catalytic enantioselective total synthesis of (+)-eucomic acid. Tetrahedron, 72 (26). pp. 3707-3712. ISSN 0040-4020. PMCID PMC4986999. doi:10.1016/j.tet.2016.02.059. https://resolver.caltech.edu/CaltechAUTHORS:20160707-080125930

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Abstract

A catalytic enantioselective synthesis of (+)-eucomic acid is reported. A palladium-catalyzed asymmetric allylic alkylation is employed to access the chiral tetrasubstituted α-hydroxyacid moiety found in the natural product. The protecting group strategy was investigated, and a protecting group manipulation was made without any appreciable deleterious effects in the allylic alkylation reaction. Non-natural (+)-eucomic acid is synthesized in a longest linear sequence of 13 steps.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/j.tet.2016.02.059DOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4986999/PubMed CentralArticle
ORCID:
AuthorORCID
Pritchett, Beau P.0000-0001-9922-9160
Craig, Robert A., II0000-0002-2435-1564
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2016 Elsevier Ltd. Received 21 January 2016; Received in revised form 24 February 2016; Accepted 25 February 2016; Available online 2 March 2016. The authors wish to thank NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, the Caltech Center for Catalysis and Chemical Synthesis, and Caltech for financial support. B.I.E. thanks the Caltech Summer Undergraduate Research Fellowship (SURF) program for summer research funding. B.P.P. thanks the NSF for a predoctoral fellowship. R.A.C. gratefully acknowledges the support of this work provided by a predoctoral fellowship from the National Cancer Institute of the National Institutes of Health under Award No. F31A17435. The authors thank Dr. Mona Shahgholi and Naseem Torian for mass spectrometry assistance and Dr. Scott C. Virgil (Caltech) for instrumentation assistance.
Funders:
Funding AgencyGrant Number
NIHR01GM080269-01
AmgenUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
NSFUNSPECIFIED
NIH Predoctoral FellowshipF31A174359
Subject Keywords:Allylic alkylation; Enantioselective; Eucomic acid; Palladium; Total synthesis
Issue or Number:26
PubMed Central ID:PMC4986999
DOI:10.1016/j.tet.2016.02.059
Record Number:CaltechAUTHORS:20160707-080125930
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160707-080125930
Official Citation:Benzi I. Estipona, Beau P. Pritchett, Robert A. Craig II, Brian M. Stoltz, Catalytic enantioselective total synthesis of (+)-eucomic acid, Tetrahedron, Volume 72, Issue 26, 30 June 2016, Pages 3707-3712, ISSN 0040-4020, http://dx.doi.org/10.1016/j.tet.2016.02.059.
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:68874
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:07 Jul 2016 20:30
Last Modified:06 May 2022 16:46

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