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Published June 30, 2016 | Supplemental Material + Accepted Version
Journal Article Open

Catalytic enantioselective total synthesis of (+)-eucomic acid


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.

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.

Attached Files

Accepted Version - nihms773128.pdf

Supplemental Material - mmc1.pdf


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