title: Studies on the total synthesis of disorazole C1. An advanced macrocycle intermediate.
abstract: Synthesis of protected tetradehydro-(6,6'-S)-(14,14'-S)-(16,16'-R)-disorazole (3), a potential precursor to the natural product disorazole C1 (1), is described. Key features of this work include (a) an unprecedented sequential 1,5 O --> O silyl rearrangement/Horner-Wadsworth-Emmons reaction used to construct 18, (b) a highly convergent Sonogashira reaction between the dienyl iodide 7 and the alkyne 8 to assemble the dienyne monomeric fragment 5, and (c) the selective cyclization of 5 to give either the cyclic monomer 23 or the dimer 3.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: M C
authors.initials: MC
authors.lastname: Hillier
authors.forename: A T
authors.initials: AT
authors.lastname: Price
authors.forename: A I
authors.initials: AI
authors.lastname: Meyers
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis*; D018942:Macrolides; D010080:Oxazoles / Q000138:chemical synthesis*
chemical_list: D000935:Antifungal Agents; D018942:Macrolides; D010080:Oxazoles; C436383:disorazole C1