光学活性倍半萜β-桉烯类似物的合成及结构分析研究

THE SYNTHESIS OF OPTICAL ACTIVE ANALOGUE OF β-SELINENE AND THE STUDY ON ITS STRUCTURE

本文叙述了具有光学活性的倍半萜β-桉烯脱甲基类似物-(+)-9β-(2′-丙烯基)-2-羟基-2-甲基-双环[4,4,0]-1-癸烯(V),(+)-9β-(2′-丙烯基)-2-亚甲基-双环[4,4,O]-1-癸烯(Ⅵ)以及β-桉烯中间体(+)-8β-(2′-丙烯基)-1-甲基-双环[4,40]-5-癸酮(Ⅶ,Ⅶ,Ⅸ,Ⅹ)的合成。化合物(Ⅴ),(Ⅵ)迄今未见文献报道,它们的化学结构得到确证,对(Ⅵ)的合成途径及结构稳定性进行了探讨,发现其稳定性优于其同分异构体(Ⅻ).

The synthesis of optical active analogue of β-selinene, a member of the eudesmane class of sesquiterpenes, (+) -9β-(2′-propenyl)-2-hydroxy-2-methyl -bicyclo(4,4,0)-1-decanene (Ⅴ), (+) -9β- (2′-propenyl) -2-methene-bicyclo (4, 4,0)-1-decanene(Ⅵ), and β-selinene intermediate (+)-8β-(2′-propenyl)-1-methyl-5-decalone(Ⅶ,Ⅷ,Ⅸ,Ⅹ)was described in this paper.The compound (Ⅴ) and (Ⅵ) have not been reported in the literature and their structures were identified.Besides this,the synthetic routes and structure stability of compounds (Ⅵ) were also explored and it has been found that compound(Ⅵ)is more stable than its isomer(ⅩⅢ).