PRODUCTION OF 16-DEHYDRO-VITAMIN D COMPOUND

摘要

PROBLEM TO BE SOLVED: To obtain the subject compound having biological activity and useful for the treatment of skin and bone diseases, the application to beauty care and the treatment of celldifferentiation, cell-proliferation or immunological diseases including inflammatory diseases such as diabetes, hypertension, rheumatic arthritis and asthma. SOLUTION: The objective 16-dehydro-vitamin D compound of the formula IV (R1 is H or an OH-protecting group; R2 is H or OH) can be produced by reacting a compound of the formula I (Z is a straight-chain hydrocarbon group, OH, F, a 1-3C alkyl, etc.; R1 ' and R4 are each an OH-protecting group; R3 is carbamic acid ester group, etc.) with a copper compound reagent to obtain a compound of the formula II (R is a 1-6C alkyl, a 2-6C alkenyl, a 3-6C cycloalkyl, etc.), deprotecting the R4 group, oxidizing the OH group to a keto group, rearranging the obtained keto compound with a Wittig reagent of the formula III (A and B are each H, methyl, etc.; R2 ' is H or an OH-protecting group; R5 is an OHprotecting group), subjecting the product to hydrogenation and isomerization and finally deprotecting the hydroxy group.