title: Phorboxazole synthetic studies. 1. Construction of a C(3-19) subtarget exploiting an extension of the Petasis-Ferrier rearrangement.
abstract: [formula: see text] In this, the first of two letters, we outline our overall strategy for the total synthesis of phorboxazoles A (1) and B (2), rare oxazole-containing macrolides possessing extraordinary antimitotic activity, and describe the assembly of a C(3-19) subtarget (-)-5 for the total synthesis of phorboxazole A. The synthesis of (-)-5 was achieved in 15 linear steps (12% overall yield), exploiting a modification of the Petasis-Ferrier rearrangement to construct the C(11-15) cis-tetrahydropyran. Dimethylaluminum chloride (Me2AlCl) proved to be the Lewis acid of choice for the Petasis-Ferrier rearrangement.
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia 19104, USA. smithab@sas.upenn.edu
authors.forename: A B
authors.initials: AB
authors.lastname: Smith
authors.forename: P R
authors.initials: PR
authors.lastname: Verhoest
authors.forename: K P
authors.initials: KP
authors.lastname: Minbiole
authors.forename: J J
authors.initials: JJ
authors.lastname: Lim
mesh_terms: D000143:Acids / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D010080:Oxazoles / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
chemical_list: D000143:Acids; D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; C408887:phorboxazole A