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A Concise Total Synthesis of (--)-Maoecrystal Z

Cha, Jacob Y. and Yeoman, John T. S. and Reisman, Sarah E. (2011) A Concise Total Synthesis of (--)-Maoecrystal Z. Journal of the American Chemical Society, 133 (38). pp. 14964-14967. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20111031-072905834

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Abstract

The first total synthesis of (--)-maoecrystal Z is described. The key steps of the synthesis include a diastereoselective Ti^(III)-mediated reductive epoxide coupling reaction and a diastereoselective Sm^(II)-mediated reductive cascade cyclization reaction. These transformations enabled the preparation of (--)-maoecrystal Z in only 12 steps from (--)-γ-cyclogeraniol.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja2073356 DOIArticle
http://pubs.acs.org/doi/full/10.1021/ja2073356PublisherArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2011 American Chemical Society. Received: August 4, 2011. Publication Date (Web): August 30, 2011. We thank Dr. Michael Day and Mr. Larry Henling for X-ray crystallographic structure determination and Dr. David Vander-Velde for assistance with NMR structure determination. We thank Prof. Brian Stoltz and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment and Dr. Scott Virgil for insightful discussions. 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). Financial support from the California Institute of Technology is gratefully acknowledged.
Funders:
Funding AgencyGrant Number
NSFCHE-0639094
CaltechUNSPECIFIED
Issue or Number:38
Record Number:CaltechAUTHORS:20111031-072905834
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20111031-072905834
Official Citation:A Concise Total Synthesis of (−)-Maoecrystal Z Jacob Y. Cha, John T. S. Yeoman, and Sarah E. Reisman Journal of the American Chemical Society 2011 133 (38), 14964-14967
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:27507
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:31 Oct 2011 15:02
Last Modified:03 Oct 2019 03:24

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