Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide

作者：Wang Shao Min; Zhang Yan Bing; Liu Hong Min^*; Yu Guo Bin; Wang Ke Rang

来源：Steroids, 2007, 72(1): 26-30.

DOI：10.1016/j.steroids.2006.10.004

• diterpene
• dibutyltin oxide
• deacetylation
• regioselective reaction

Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization nor degradation of these substrates was observed. It seems that the acetyl groups with lower steric hindrance or near carbonyl, alkoxy, or hydroxyl groups can be cleaved by the reaction, whereas the acetyl groups with higher steric hindrance or without carbonyl, alkoxy, or hydroxyl groups neighboring were retained under the same conditions. One of the interesting results obtained was the selective hydrolysis of the 3 beta-O-acetyl group in the presence of the 6 beta group in 3 beta,6 beta-Di-O-acetyl-5 alpha-hydroxypregn-16-en-20-one. This allows for subsequent introduction of one unit at C-3 and the other unit at C-6. This procedure is useful for the synthesis of a series of closely related isomers of 3 beta, 5 alpha, 6 beta-trihydroxypregn-16-en-20-one and other widespread polyhydroxysteroids in marine organisms and some terrestrial species.

• 出版日期2007-1
• 单位郑州大学