高等学校化学学报

高等学校化学学报 ›› 1996, Vol. 17 ›› Issue (11): 1734.

• 论文 • 上一篇    下一篇

(±)-表-马氏醇的合成(Ⅱ)

王贵阳生, 苏镜娱, 曾陇梅   

  1. 中山大学化学系, 广州, 510275
  • 收稿日期:1995-12-04 出版日期:1996-11-24 发布日期:1996-11-24
  • 通讯作者: 曾陇梅
  • 作者简介:王贵阳生,男,33岁,博士,讲师.
  • 基金资助:

    国家自然科学基金;国家教育委员会博士学科点专项基金

The Total Synthesis of (±)-Epi-mayol(Ⅱ)

WANG Gui-Yang-Sheng, SU Jing-Yu, ZENG Long-Mei   

  1. Department of Chemistry, Zhongshan University, Guangzhou, 510275
  • Received:1995-12-04 Online:1996-11-24 Published:1996-11-24

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摘要： 报道了(±)-表-马氏醇的另一种合成方法。应用羟基香叶醛及芳樟醇为原料,通过关键中间体(2E,6E,10E,14E)-16-羟基-3,7,11,15-四甲基-9-苯磺酰基-2,6,10,14-十六碳四烯醛及溴化物,在无水CrCl2作用下,分子内缩合生成苏式醇为主的环化产物(大环二萜).将大环二萜用钠汞齐脱除苯磺酸酯得(±)-表-马氏醇,总产率为8.5%.

关键词: 二萜, 表-马氏醇, 反-15, 16-去氢苜枯醇, 反-1-羟基-新西松烯, 缩合

Abstract: The total synthesis of(±)-epi-mayol(1)using hydroxygeranial(2)and linalool (5)as starting material was described.2,6-Dimethyl-8,8-diethoxy-octa-2,6-dieneyl-p-tosylate(4)was prepared from(2),and 8-hydroxy-3,7-dimethyl-octa-2,6-dieneyl-phenylsulfone(7)was prepared from(5).Then(4)and(7)were condensed in the presence of NaNH2 afford to the intermediate 16-hydroxy-3,7,11,15-tetramethyl-9-phenylsulfonyl-hexadeca-2,6,10,14-tetraene-al(8).8 was converted to bromide(9)and followed by ring closure in the presence of Cr(Ⅱ)to form a macrocyclic diterpene.The resulted mixture was purified by flash chromatography with high performance silicagel to obtain pure(10).Finally,the sulfonyl group of 10 was eliminated by sodium amalgam to give 1 in 8.5% overall yield.

Key words: Diterpene, Epi-mayol, 16-Dehydro-mukurol, E-1-Hydroxy-neocembrene, Condensation

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