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Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (–)-3-demethoxyerythratidinone

Chuang, Kangway V. and Navarro, Raul and Reisman, Sarah E. (2011) Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (–)-3-demethoxyerythratidinone. Chemical Science, 2 (6). pp. 1086-1089. ISSN 2041-6520 . https://resolver.caltech.edu/CaltechAUTHORS:20110606-112443200

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Abstract

The preparation and synthetic applications of benzoquinone monoketal-derived N-tert-butanesulfinyl imines is described. These synthetically versatile intermediates undergo highly diastereoselective 1,2-addition reactions with organometallic reagents to provide 4-aminocyclohexadienones in good yields. The utility of this methodology is demonstrated in a six-step enantioselective synthesis of (–)-3-demethoxyerythratidinone.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1039/C1SC00095KDOIArticle
http://pubs.rsc.org/en/Content/ArticleLanding/2011/SC/c1sc00095kPublisherArticle
ORCID:
AuthorORCID
Chuang, Kangway V.0000-0002-0652-8071
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2011 The Royal Society of Chemistry. Received 16th February 2011, Accepted 25th February 2011. First published on the web 25 Mar 2011. We thank Drs. Michael Day and Larry Henling for X-ray crystallographic structural 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 thank the Gates Millennium Scholars Program (R.N.) and the Amgen Scholars Program (K.V.C.) for fellowship support. Andrew Lim is acknowledged for assistance in the preparation of compound 10. HRMS and X-ray crystallographic data were obtained on instruments purchased through awards to the California Institute of Technology by the NSF CRIF program (CHE-0639094, CHE-0541745). Financial support from the California Institute of Technology is gratefully acknowledged.
Funders:
Funding AgencyGrant Number
Bill and Melinda Gates FoundationUNSPECIFIED
AmgenUNSPECIFIED
NSFCHE-0639094
NSFCHE-0541745
CaltechUNSPECIFIED
Issue or Number:6
Record Number:CaltechAUTHORS:20110606-112443200
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20110606-112443200
Official Citation:Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (–)-3-demethoxyerythratidinone Kangway V. Chuang, Raul Navarro and Sarah E. Reisman Chem. Sci., 2011, 2, 1086-1089 DOI: 10.1039/C1SC00095K
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:23916
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:06 Jun 2011 18:49
Last Modified:03 Oct 2019 02:51

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