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Diverging stereochemical pathways in an intramolecular Diels-Alder reaction determined by dienophile structure.

Authors :
Kim K
Maharoof US
Raushel J
Sulikowski GA
Source :
Organic letters [Org Lett] 2003 Aug 07; Vol. 5 (16), pp. 2777-80.
Publication Year :
2003

Abstract

[reaction: see text] Intramolecular Diels-Alder cycloaddition of tolylsulfonyl alkynone 5a and vinyl ketone 19 led to single isomers with opposite diastereoselectivity. Decalin 20 incorporates the correct C(9)-C(11) stereochemical array for a projected synthesis of HMP-Y1 (1).

Details

Language :
English
ISSN :
1523-7060
Volume :
5
Issue :
16
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
12889872
Full Text :
https://doi.org/10.1021/ol034823f