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Paper | Regular issue | Vol 68, No. 12, 2006, pp.2509-2514
Published online, 31st October, 2006
DOI: 10.3987/COM-06-10875
Total Inversion of Cis-C5 Maxacalcitol into Its Trans-C5 Isomer via the Sulforene Intermediate

Tsuyoshi Yamauchi,* Koji Suzuki, Hitoshi Shimizu, and Masahiro Kato

*Pre-Clinical Research Department I, Fuji-gotemba Research Laboratories, Chugai Pharmaceutical Company, Ltd., 135, 1-Chome Komakado, Gotemba City, Shizuoka 412-8513, Japan


Total inversion of the cis-C5 configuration of Maxacalcitol, the unnatural 22-oxa-vitamin D3 analogue used for the treatment of secondary hyperparathyroidism and psoriasis, into the trans-C5 isomer has been accomplished stereoselectively via a formation of the sulforene intermediate for biological evaluation.