title: A formal total synthesis of the salicylihalamides.
abstract: The synthesis of the macrolactone 23 is described. The synthesis features a diastereoselective hydroboration of the chiral alkene 17 followed by a Suzuki cross-coupling reaction with the benzoate 5. The resulting seco acid 21 was converted to the macrolactone 23 by a Mitsunobu lactonization using immobilized triphenylphosphine. The stereogenic centers in the alkene 17 were established by a Noyori reduction of the beta-keto ester 8 and an Evans aldol reaction. The synthesis illustrates the conversion of a syn aldol product to the corresponding anti product by inversion of the methyl-bearing center.
authors.affiliation: Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Herb
authors.forename: Martin E
authors.initials: ME
authors.lastname: Maier