Enantioselective syntheses of colletodiol, colletol, and grahamimycin A.
[reaction: see text] The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.
Hunter
Thomas J
TJ
Department of Chemistry, West Virginia University, Morgantown 26506, USA.
O'Doherty
George A
GA
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D005658:Fungi / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000438:Alcohols; D007783:Lactones; C470815:colletol; C111697:colletodiol; C030402:grahamimycin A