title: Remote asymmetric induction in an intramolecular ionic Diels-Alder reaction: application to the total synthesis of (+)-dihydrocompactin.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309-0215, USA. Sammakia@colorado.edu
authors.forename: Tarek
authors.initials: T
authors.lastname: Sammakia
authors.forename: Deidre M
authors.initials: DM
authors.lastname: Johns
authors.forename: Ganghyeok
authors.initials: G
authors.lastname: Kim
authors.forename: Martin A
authors.initials: MA
authors.lastname: Berliner
mesh_terms: D007477:Ions; D008148:Lovastatin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D007477:Ions; C031380:dihydrocompactin; D008148:Lovastatin