Allylic alcohol transposition by ortho ester-initiated carbonate extension. synthesis of the vasodilator 11(R),12(S),15(S)-trihydroxyeicosa- 5(Z),8(Z),13(E)-trienoic acid.
[reaction: see text] The title compound 1 was obtained via methyl ester 2, which was synthesized in four steps from an isomeric 11,14,15-triol ester 5. In the key step, Boc orthoformate 9 was treated with TMS triflate to initiate intramolecular nucleophilic substitution with allylic transposition, forming cyclic carbonates 10 and 11.
Conrow
Raymond E
RE
Alcon Research, Ltd., Chemical Preparations Research, Fort Worth, Texas 76134, USA. ray.conrow@alconlabs.com
D015126:8,11,14-Eicosatrienoic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry; D014665:Vasodilator Agents / Q000138:chemical synthesis*
D002254:Carbonates; D004952:Esters; D020005:Propanols; D014665:Vasodilator Agents; C006463:allyl alcohol; C066049:11,12,15-trihydroxyeicosatrienoic acid; D015126:8,11,14-Eicosatrienoic Acid