A straightforward route to functionalized trans-Diels-Alder motifs.
A sequence consisting of a Lewis acid-catalyzed Diels-Alder reaction on a 2-halocyclohexenone, followed by reductive alkylation, provides a route to trans-fused octalinones bearing angular methyl groups with functionality corresponding to that which would have been possible from a trans-directed Diels-Alder reaction.
Lee
Jun Hee
JH
Department of Chemistry, Havemeyer Hall, Columbia University, 3000 Broadway, New York, New York 10027, USA.
Zhang
Yandong
Y
Danishefsky
Samuel J
SJ
D000478:Alkylation; D002384:Catalysis; D053138:Cyclohexenes / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry*; D010084:Oxidation-Reduction
D053138:Cyclohexenes; D058116:Lewis Acids