Published May 16, 2011
| Published + Supplemental Material
Journal Article
Open
Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (–)-3-demethoxyerythratidinone
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.
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.Attached Files
Published - Chuang2011p14036Chem_Sci.pdf
Supplemental Material - c1sc00095k.pdf
Supplemental Material - c1sc00095k.txt
Files
Chuang2011p14036Chem_Sci.pdf
Additional details
- Eprint ID
- 23916
- Resolver ID
- CaltechAUTHORS:20110606-112443200
- Bill and Melinda Gates Foundation
- Amgen
- CHE-0639094
- NSF
- CHE-0541745
- NSF
- Caltech
- Created
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2011-06-06Created from EPrint's datestamp field
- Updated
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2021-11-09Created from EPrint's last_modified field