有机化学 ›› 1987, Vol. 7 ›› Issue (5): 354-356. 上一篇    下一篇

研究论文

内分子DIELS-ALDER反应合成DRIMANE类倍半萜化合物DRIMENIN, POLYGODIAL及CINNAMOLIDE的全合成

贺菊芳;吴毓林   

  1. 中国科学院上海有机化学研究所
  • 发布日期:1987-10-25

The intramolecular Diels-Alder approach to drimane related sesquiterpenes synthesis of drimenin, polygodial and cinnamolide

HE JUFONG;WU YULIN   

  • Published:1987-10-25

近年来有不少报道从事于生理活性Drimane类倍半萜的合成[1],较多采用了分子间Diels-Alder反应来建立Drimane的骨架。本文首次采用内分子Diels-Alder反应作为关键反应合成了Drimane类化合物。同时还在引入了手性诱导基团后,首次完成了从无手性的原料化合物β-紫罗兰酮至光学活性(-)-drimenin 1的不对称合成。

关键词: 内酯, 呋喃酮 P, 倍半萜, 十氢化萘 P, 萘甲酸 P, 迪尔斯-阿尔德反应

Drimane sesquiterpenes were prepared via an intramol. Diels-Alder reaction of b-ionone derivative I to by intermediate II. Reduction, lactonization, hydrogenation and dehydroxymethylation of II gave (?-drimenin (III; RR = O, R1 = H). (?-Polgodial (IV) and (?-cinnamolide (III; R = H, R1R1 = O) were then prepared from III (RR = O, R1 = H) via reduction and oxidation

Key words: LACTONES, FURANONE P, SESQUITERPENE, DECALIN P, NAPHTHALENECARBOXYLIC ACID P, DIELS-ALDER REACTION

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