Studies on the total synthesis of disorazole C1. An advanced macrocycle intermediate.
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.
Hillier
M C
MC
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Price
A T
AT
Meyers
A I
AI
D000935:Antifungal Agents / Q000138:chemical synthesis*; D018942:Macrolides; D010080:Oxazoles / Q000138:chemical synthesis*
D000935:Antifungal Agents; D018942:Macrolides; D010080:Oxazoles; C436383:disorazole C1