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From natural camphor to (1R,2S)-2-chloromethyl-3-oxocyclopentanecarboxylic acid: a stereocontrolled approach to enantiopure sarkomycin

✍ Scribed by Antonio Garcı́a Martı́nez; Enrique Teso Vilar; Amelia Garcı́a Fraile; Santiago de la Moya Cerero; Sergio de Oro Osuna; Beatriz Lora Maroto

Book ID
104231711
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
192 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

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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