Author/Authors :
Garc??a Mart??nez، نويسنده , , Antonio and Teso Vilar، نويسنده , , Enrique and Garc??a Fraile، نويسنده , , Amelia and de la Moya Cerero، نويسنده , , Santiago and de Oro Osuna، نويسنده , , Sergio and Lora Maroto، نويسنده , , Beatriz، نويسنده ,
Abstract :
The preparation of enantiopure (1R,2S)-2-chloromethyl-3-oxocyclopentanecarboxylic acid 9, an interesting possible precursor of the antitumor agent sarkomycin, from a camphor-derived 3-hydroxymethylnorbornan-2-one is reported. The described procedure constitutes the first stereocontrolled approach to sarkomycin starting from commercially available natural camphor. The procedure takes place in only six steps with a high overall yield (59%). The key-step of the described procedure is the stereocontrolled ring opening of a conveniently functionalized 3-oxonorborn-1-yl triflate under a straightforward basic hydrolysis. The described route constitutes a model procedure for the preparation of other enantiopure C2-substituted 3-oxocyclopentanecarboxylic acids; which are related with the sarkomycin family of antitumor agents.
