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Dimethyl (R)S-2-(10-isobornylsulfinyl)maleate, a chiral synthetic equivalent of dimethyl acetylenedicarboxylate: Preparation and its application to the formal chiral synthesis of (-)-neplanocin A and (-)-aristeromycin

✍ Scribed by Yoshitsugu Arai; Kazuya Hayashi; Toru Koizumi; Motoo Shiro; Kaoru Kuriyama

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 292 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)82289-3

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✦ Synopsis

A novel chiral synthetic equivalent of dimethyl acetylenedicarboxylate, dimethyl (R)S-2-(10-isobornylsulfinyl)maleate (3), was synthesized. Diels-Alder reaction of (3) with cyclopentadiene proceeded with high stereoand diastereo-selectivity to afford the cycloadduct (4) almost exclusively, which has been transformed into the half-ester (71, an intermediate in the synthesis of (-)-aristeromycin and (-)-neplanocin A.

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