Diverging stereochemical pathways in an intramolecular Diels-Alder reaction determined by dienophile structure.
[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).
Kim
Kwangho
K
Department of Chemistry, Texas A&M University, College Station, Texas 77842, USA.
Maharoof
Umar S M
US
Raushel
Jessica
J
Sulikowski
Gary A
GA
D015394:Molecular Structure; D013237:Stereoisomerism