title: 1,6-asymmetric induction in boron-mediated aldol reactions: application to a practical total synthesis of (+)-discodermolide.
abstract: By relying solely on substrate-based stereocontrol, a practical total synthesis of the microtubule-stabilizing anticancer agent (+)-discodermolide has been realized. This exploits a novel aldol bond construction with 1,6-stereoinduction from the boron enolate of (Z)-enone 3 in addition to aldehyde 2. The 1,3-diol 7 is employed as a common building block for the C(1)-C(5), C(9)-C(16), and C(17)-C(24) subunits. [reaction--see text]
authors.affiliation: University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U.K. ip100@cus.cam.ac.uk
authors.forename: Ian
authors.initials: I
authors.lastname: Paterson
authors.forename: Oscar
authors.initials: O
authors.lastname: Delgado
authors.forename: Gordon J
authors.initials: GJ
authors.lastname: Florence
authors.forename: Isabelle
authors.initials: I
authors.lastname: Lyothier
authors.forename: Jeremy P
authors.initials: JP
authors.lastname: Scott
authors.forename: Natascha
authors.initials: N
authors.lastname: Sereinig
mesh_terms: D000473:Alkanes; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001895:Boron / Q000737:chemistry*; D002219:Carbamates; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera; D011753:Pyrones
chemical_list: D000473:Alkanes; D000970:Antineoplastic Agents; D002219:Carbamates; D007783:Lactones; D011753:Pyrones; C071229:discodermolide; D001895:Boron