Published December 23, 2013
| Version 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
Creators
Abstract
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
Files
chem_201302353_sm_miscellaneous_information.pdf
Additional details
Identifiers
- PMCID
- PMC3927641
- Eprint ID
- 42896
- DOI
- 10.1002/chem.201302353
- Resolver ID
- CaltechAUTHORS:20131209-101849386
Funding
- NIH
- R01 M080269
- Amgen
- Gordon and Betty Moore Foundation
- ARCS Foundation
- Caltech
Dates
- Created
-
2013-12-11Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field