Issue 6, 2011
From the journal:

Chemical Science

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

Kangway V. Chuang,a   Raul Navarroa  and  Sarah E. Reisman*a  

* Corresponding authors

a The Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, USA
E-mail: reisman@caltech.edu

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.

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

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Article information

DOI
https://doi.org/10.1039/C1SC00095K
Article type
Edge Article
Submitted
16 Feb 2011
Accepted
25 Feb 2011
First published
25 Mar 2011

Chem. Sci., 2011,2, 1086-1089

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

K. V. Chuang, R. Navarro and S. E. Reisman, Chem. Sci., 2011, 2, 1086 DOI: 10.1039/C1SC00095K

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