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Paper | Regular issue | Vol 65, No. 9, 2005, pp.2107-2118
Published online, 26th July, 2005
DOI: 10.3987/COM-05-10463
Synthesis of 1-Deoxymaxacalcitol

Tsuyoshi Yamauchi,* Masahiro Kato, Tetsuhiro Mikami, and Yasuo Fujimura

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

Abstract

1-Deoxymaxacalcitol, the 1-deoxygenated derivative of maxacalcitol practically used for the treatment of secondary hyperparathyroidism and psoriasis, has been synthesized for the biological evaluation. Although purification of the key intermediate containing 1,3-cyclohexadiene moiety was extremely difficult owing to inseparable contaminants, treatment of the mixture with the heterocyclic dienophile 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) formed the readily separable Diels-Alder adduct from which the target 1-deoxymaxacalcitol could be obtained in a pure state.