Efficient chemoenzymatic synthesis of phenylacetylrinvanil: an ultrapotent capsaicinoid.

[摘要]：The straightforward synthesis of (phenylacetyl)rinvanyl (PhAR), an ultrapotent capsaicinoid is described. The process starts with the quant. synthesis of Me ricinoleate (MeRic) by castor oil methanolysis. Afterwards, two alternative routes are possible: (a) chemoselective vanillylamine aminolysis of MeRic catalyzed by Candida antarctica lipase-B (CaLB) to yield rinvanil, which after reaction with BnCO2H and DCC-DMAP followed by a regioselectively pyrrolidine deacylation results in PhAR in 51% total yield, (b) 12-phenylacetylricinoleate synthesis by reaction of MeRic with BnCO2H and DCC-DMAP, followed by a chemoselective vanillylamine aminolysis catalyzed by CaLB to obtain PhAR in 70% total yield.

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