title: Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step.
abstract: The first organocatalytic asymmetric synthesis of smyrindiol, by using an (S)-proline catalyzed enantioselective intramolecular aldol reaction as the key step, is described. Smyrindiol was synthesized from commercially available 2,4-dihydroxybenzaldehyde in 15 steps, with excellent stereoselectivity (de = 99%, ee = 99%). In the course of this total synthesis a new and mild coumarin assembly was developed.
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany.
authors.forename: Dieter
authors.initials: D
authors.lastname: Enders
authors.forename: Jeanne
authors.initials: J
authors.lastname: Fronert
authors.forename: Tom
authors.initials: T
authors.lastname: Bisschops
authors.forename: Florian
authors.initials: F
authors.lastname: Boeck