Remote asymmetric induction in an intramolecular ionic Diels-Alder reaction: application to the total synthesis of (+)-dihydrocompactin.
The total synthesis of (+)-dihydrocompactin via an intramolecular ionic Diels-Alder reaction that proceeds with remote stereocontrol is described. This reaction proceeds by an intermediate vinyl-oxocarbenium ion (6), the conformational constraints of which lead to the observed asymmetric induction. The sense of asymmetric induction appears contrasteric and is explained by the proposed reactive conformation shown in Figure 1.
Sammakia
Tarek
T
Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309-0215, USA. Sammakia@colorado.edu
Johns
Deidre M
DM
Kim
Ganghyeok
G
Berliner
Martin A
MA
D007477:Ions; D008148:Lovastatin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D007477:Ions; C031380:dihydrocompactin; D008148:Lovastatin