Versatile synthesis of the C3-C14 domain of 7-deoxyokadaic acid.
Described is a flexible synthesis of the C3-C14 domain of 7-deoxyokadaic acid that is amenable to facile structural diversification. Treatment of ynone 10 under acidic conditions led to net bis-conjugate addition of the latent diol to give the thermodynamically favored spiroketal 27, a versatile intermediate, en route to 7-deoxyokadaic acid and analogs.
Trygstad
Timothy M
TM
Department of Chemistry and Physical Sciences, The College of St. Scholastica, Duluth, Minnesota 55811, USA.
Pang
Yucheng
Y
Forsyth
Craig J
CJ
D018360:Crystallography, X-Ray; D019319:Okadaic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D010744:Phosphoric Monoester Hydrolases / Q000378:metabolism
C538742:7-deoxyokadaic acid; D019319:Okadaic Acid; D010744:Phosphoric Monoester Hydrolases