Jump to main content
Jump to site search

Issue 6, 2011
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 16 Feb 2011, accepted on 25 Feb 2011, published on 25 Mar 2011 and first published online on 25 Mar 2011


Article type: Edge Article
DOI: 10.1039/C1SC00095K
Citation: Chem. Sci., 2011,2, 1086-1089
  •   Request permissions

    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

Search articles by author