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Citation: HE Shi-Hua. Convenient and High Efficient Synthesis of 15β,16β-Methylen-androsta-5-en-3β-ol-17-one[J]. Chinese Journal of Applied Chemistry, ;2009, 26(4): 405-408. shu

Convenient and High Efficient Synthesis of 15β,16β-Methylen-androsta-5-en-3β-ol-17-one

HE Shi-Hua ^,

1.
Department of Chemistry and Chemical Engineering, Xi'an University of Science and Technology, Xi'an 710054

Corresponding author: HE Shi-Hua,
Received Date: 26 March 2008
Available Online: 26 June 2008

With paratoluenesulfonic acid(pTsOH) or trifluoroacetic acid(TFA) as catalyst,3β-acetoxy-androsta-5,15-dien-17-one(Ⅰ) was conveniently and efficiently obtained from o-iodoxybenzoic acid(IBX) selective dehydrogenation to dehydroepiandrosterone acetate in Tol-DMSO at 40~45 ℃in the yields of 77% and 89%,respectively.The synthetic routes avoided the disadvantages of bromination-debromination and fermentation route,i.e.,too many reaction steps,higher toxicity,larger costs,as well as the shortcomings of simple IBX selective dehydrogenation such as higher reaction temperature,longer reaction time.Hydrolysis of compoundⅠ by strong base gave 3β-hydroxyl-androsta-5,15-dien-17-one(Ⅱ) in a yield of 92%.The target 15β,16β-methylen-androsta-5-en-3β-ol-17-one(Ⅲ) was synthesized from Compound Ⅱ through Michaels' conjugate addition with trime-thylsulfoxonium iodide in THF-DMSO at 12~20 ℃ in a yield of 89%.The chemical structures of intermediates and target product were characterized by UV,IR,¹H NMR,MS,and elemental analysis.
- dehydroepiandrosterone acetate,
- IBX,
- 15β,16β-methylen-androsta-en-3β-ol-one,
- α,β-unsaturated carbonyl steroid,
- intermediates
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