title: Total synthesis of the cytotoxic enehydrazide natural products hydrazidomycins A and B by a carbazate addition/Peterson olefination approach.
abstract: The first total syntheses of two natural antitumor enehydrazide compounds (hydrazidomycins A and B) and a related positional isomer of hydrazidomycin B (elaiomycin B) have been accomplished in a rapid and stereocontrolled fashion using a Peterson elimination approach. A regioselective silyl epoxide ring opening reaction with Boc-carbazate followed by base-mediated Peterson siloxide elimination stereospecifically installed the key Z-enehydrazide functionality. The use of Boc-carbazate allowed for the differential functionalization of the hydrazide nitrogens.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto ON, Canada.
authors.forename: Ramsay E
authors.initials: RE
authors.lastname: Beveridge
authors.forename: Robert A
authors.initials: RA
authors.lastname: Batey
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006834:Hydrazines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000970:Antineoplastic Agents; D001688:Biological Products; D006834:Hydrazines; C557938:elaiomycin B; C571359:hydrazidomycin A; C010877:carbazic acid