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A Unified Strategy to ent-Kauranoid Natural Products: Total Syntheses of (−)-Trichorabdal A and (−)-Longikaurin E

Yeoman, John T. S. and Mak, Victor W. and Reisman, Sarah E. (2013) A Unified Strategy to ent-Kauranoid Natural Products: Total Syntheses of (−)-Trichorabdal A and (−)-Longikaurin E. Journal of the American Chemical Society, 135 (32). pp. 11764-11767. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20130913-104221740

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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.


Item Type:Article
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URLURL TypeDescription
http://dx.doi.org/10.1021/ja406599a DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja406599aPublisherArticle
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.
Funders:
Funding AgencyGrant Number
Bristol-Myers Squibb UNSPECIFIED
NSFDGE-1144469
CaltechUNSPECIFIED
Amgen UNSPECIFIED
Alfred P. Sloan FoundationUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Record Number:CaltechAUTHORS:20130913-104221740
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20130913-104221740
Official Citation:A Unified Strategy to ent-Kauranoid Natural Products: Total Syntheses of (−)-Trichorabdal A and (−)-Longikaurin E John T. S. Yeoman, Victor W. Mak, and Sarah E. Reisman Journal of the American Chemical Society 2013 135 (32), 11764-11767
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:41318
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:16 Sep 2013 21:14
Last Modified:16 Sep 2013 21:14

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