Versatile synthesis and biological evaluation of 1, 3-diamino-substituted 1α, 25-dihydroxyvitamin D 3 analogues

…, S Fernández, M Ferrero, R Bouillon, A Verstuyf…

Index: Oves, Daniel; Fernandez, Susana; Ferrero, Miguel; Bouillon, Roger; Verstuyf, Annemieke; Gotor, Vicente Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 4 p. 928 - 937

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Citation Number: 8

Abstract

A concise route to 1α, 3β-diamino-25-hydroxy-3-deoxyvitamin D3 (5) and 1β, 3α-diamino-25- hydroxy-3-deoxyvitamin D3 (6) has been developed starting from (R)-or (S)-carvone for the construction of the modified A-ring fragments. The conversion of the hydroxyl group to amine function with complete inversion of the configuration was efficiently accomplished by Mitsunobu reaction using phthalimide as nucleophile or activation of the hydroxyl group ...