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A unified strategy for the synthesis of (−)-maoecrystal Z, (−)-trichorabdal A, and (−)-longikaurin E

Yeoman, John T. S. and Cha, Jacob Y. and Mak, Victor W. and Reisman, Sarah E. (2014) A unified strategy for the synthesis of (−)-maoecrystal Z, (−)-trichorabdal A, and (−)-longikaurin E. Tetrahedron, 70 (27-28). pp. 4070-4088. ISSN 0040-4020. doi:10.1016/j.tet.2014.03.071.

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Herein we describe in full our investigations that led to the completion of the first total syntheses of (−)-maoecrystal Z, (−)-trichorabdal A, and (−)-longikaurin E. The unified strategy employs a Ti^(III)-mediated reductive epoxide coupling to rapidly prepare a key spirolactone. Highly diastereoselective Sm^(II)-mediated reductive cyclizations and a Pd^(II)-mediated oxidative cyclization enable the construction of three architecturally distinct ent-kauranoid frameworks from this common intermediate.

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Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2014 Elsevier Ltd. Received 19 February 2014; Received in revised form 17 March 2014; Accepted 21 March 2014; Available online 29 March 2014. We thank Mr. Larry Henling and the late Dr. Michael Day for X-ray crystallographic structure determination and Dr. David VanderVelde for assistance with NMR structure determination. We also thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, as well as Sigmae-Aldrich for a kind donation of chemicals. The Bruker KAPPA APEXII X-ray diffractometer was purchased through an award to the California Institute of Technology by the NSF CRIF program (CHE-0639094). S.E.R. is a fellow of the Alfred P. Sloan Foundation, a Camille Dreyfus Teacher-Scholar, and an American Cancer Society Research Scholar. Fellowship support from Bristol-Myers Squibb (_100002491) (J.T.S.Y.) and the National Science Foundation (_100000001) (Graduate Research Fellowship, V.W.M., Grant No. DGE-1144469) and financial support from the California Institute of Technology, the National Science Foundation (CAREER-1057143), Boehringer Ingelheim (_100001003), and Amgen (_100002429) are gratefully acknowledged.
Funding AgencyGrant Number
Alfred P. Sloan FoundationUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
American Cancer SocietyUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
NSF Graduate Research FellowshipDGE-1144469
Boehringer IngelheimUNSPECIFIED
Issue or Number:27-28
Record Number:CaltechAUTHORS:20140725-092716157
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Official Citation:John T.S. Yeoman, Jacob Y. Cha, Victor W. Mak, Sarah E. Reisman, A unified strategy for the synthesis of (−)-maoecrystal Z, (−)-trichorabdal A, and (−)-longikaurin E, Tetrahedron, Volume 70, Issues 27–28, 8 July 2014, Pages 4070-4088, ISSN 0040-4020, (
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:47494
Deposited By: Tony Diaz
Deposited On:25 Jul 2014 17:14
Last Modified:10 Nov 2021 17:40

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