title: Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions.
abstract: The marine natural product (+)-discodermolide was first isolated in 1990 and, to this day, remains a compelling synthesis target. Not only does the compound possess fascinating biological activity, but it also presents an opportunity to test current methods for chemical synthesis and provides an inspiration for new reaction development. A new synthesis of discodermolide employs a previously undisclosed stereoselective catalytic diene hydroboration and also establishes a strategy for the alkylation of chiral enolates. Furthermore, this synthesis of discodermolide provides the first examples of the asymmetric 1,4-diboration of dienes and borylative diene-aldehyde couplings in complex-molecule synthesis.
authors.affiliation: Department of Chemistry, Boston College, Merkert Research Labs, 2609 Beacon Street, Chestnut Hill, MA 02467 (USA).
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Yu
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Ely
authors.forename: James P
authors.initials: JP
authors.lastname: Morken
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D001895:Boron / Q000737:chemistry*; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D002219:Carbamates; D007783:Lactones; D011753:Pyrones; C071229:discodermolide; D001895:Boron
keywords: asymmetric catalysis; diboration; discodermolide; hydroboration; total synthesis