Published August 14, 2013
| Version Supplemental Material
Journal Article
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A Unified Strategy to ent-Kauranoid Natural Products: Total Syntheses of (−)-Trichorabdal A and (−)-Longikaurin E
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1.
California Institute of Technology
Abstract
The first total syntheses of (−)-trichorabdal A and (−)-longikaurin E are reported. A unified synthetic strategy is employed that relies on a Pd-mediated oxidative cyclization of a silyl ketene acetal to generate an all-carbon quaternary center and build the bicyclo[3.2.1]octane framework. These studies, taken together with our previous synthesis of (−)-maoecrystal Z, demonstrate that three architecturally distinct ent-kauranoids can be prepared from a common spirolactone intermediate.
Additional Information
© 2013 American Chemical Society. Received: June 28, 2013; Published: July 25, 2013. We thank Dr. David VanderVelde for assistance with NMR structure determination, as well as Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Sigma-Aldrich for a kind donation of chemicals. S.E.R. is a fellow of the Alfred P. Sloan Foundation and a Camille Dreyfus Teacher-Scholar. Fellowship support from Bristol-Myers Squibb (J.T.S.Y.) and the National Science Foundation (Graduate Research Fellowship, V.W.M., Grant No. DGE-1144469), and financial support from the California Institute of Technology and Amgen, are gratefully acknowledged.Attached Files
Supplemental Material - ja406599a_si_001.pdf
Supplemental Material - ja406599a_si_002.pdf
Files
ja406599a_si_001.pdf
Additional details
Identifiers
- Eprint ID
- 41318
- Resolver ID
- CaltechAUTHORS:20130913-104221740
Funding
- Bristol-Myers Squibb
- NSF
- DGE-1144469
- Caltech
- Amgen
- Alfred P. Sloan Foundation
- Camille and Henry Dreyfus Foundation
Dates
- Created
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2013-09-16Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field