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Published January 15, 2009 | Accepted Version + Supplemental Material
Journal Article Open

Enantioselective Total Synthesis of (+)-Cassiol


An enantioselective total synthesis of (+)-cassiol is reported. The complex derived from Pd-2(pmdba)(3) and enantiopure t-BuPHOX ligand catalyzes enantioconvergent decarboxylative alkylation to generate the quaternary carbon stereocenter at an early stage. The overall synthetic strategy involves a convergent late-stage coupling of two fragments. The synthesis features a longest linear sequence of eight steps.

Additional Information

© 2008 American Chemical Society. Received October 19, 2008. We thank Samantha R. Levine and Michael R. Krout (Caltech) for helpful discussions and experimental assistance. We thank the NIH-NIGMS (R01 GM080269-01), Caltech Amgen Scholars Program (undergraduate fellowship to K.V.P.), Eli Lilly (predoctoral fellowship to J.T.M.), Amgen, Bristol-Myers Squibb, Merck Research Laboratories, Abbott Laboratories, Boehringer-Ingelheim, and Caltech for financial support.

Attached Files

Accepted Version - nihms110343.pdf

Supplemental Material - PETol09supp.pdf


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