Add time:08/28/2019         Source:sciencedirect.com

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.

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