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Published December 23, 2013 | Supplemental Material + Accepted Version
Journal Article Open

A Unified Approach to the Daucane and Sphenolobane Bicyclo[5.3.0]decane Core: Enantioselective Total Syntheses of Daucene, Daucenal, Epoxydaucenal B, and 14-para-Anisoyloxydauc-4,8-diene


Access to the bicyclo[5.3.0]decane core found in the daucane and sphenolobane terpenoids via a key enone intermediate enables the enantioselective total syntheses of daucene, daucenal, epoxydaucenal B, and 14-para-anisoyloxydauc-4,8-diene. Central aspects include a catalytic asymmetric alkylation followed by a ring contraction and ring-closing metathesis to generate the five- and seven-membered rings, respectively.

Additional Information

© 2013 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim. Received: June 19, 2013. Article first published online: 2 Dec. 2013. The authors wish to thank the NIH-NIGMS (R01 M080269), Amgen, the Gordon and Betty Moore Foundation, the ARCS foundation, and Caltech for awards and financial support. Dr. Allen Hong, Dr. Thomas Jensen, and Prof. Sarah Reisman are acknowledged for helpful discussions and suggestions. Dr. David VanderVelde and Dr. Scott Ross are acknowledged for NMR spectroscopic assistance. Dr. Mona Shahgoli and Naseem Torian are acknowledged for high-resolution mass spectrometry assistance.

Attached Files

Accepted Version - nihms547975.pdf

Supplemental Material - chem_201302353_sm_miscellaneous_information.pdf


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