title: Toward the total synthesis of the brasilinolides: construction of a differentially protected C20-C38 segment.
abstract: An efficient, convergent synthesis of a differentially protected C20-C38 segment of the brasilinolides is described. Iterative 1,4-syn aldol additions and ketone reductions were employed to construct the two related stereotetrads, while a sequence of Horner-Wadsworth-Emmons (HWE) coupling, CBS reduction, and Sharpless AE installed the epoxy alcohol functionality.
authors.affiliation: University Chemical Laboratory, Lensfield Road, Cambridge, UK.
authors.forename: Ian
authors.initials: I
authors.lastname: Paterson
authors.forename: Paul M
authors.initials: PM
authors.lastname: Burton
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Cordier
authors.forename: Michael P
authors.initials: MP
authors.lastname: Housden
authors.forename: Friedrich A
authors.initials: FA
authors.lastname: Mühlthau
authors.forename: Olivier
authors.initials: O
authors.lastname: Loiseleur
mesh_terms: D002384:Catalysis; D007659:Ketones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D018942:Macrolides; D011714:Pyrans; C111141:brasilinolide A; C406050:brasilinolide B; C484617:brasilinolide C