Common synthetic strategy for optically active cyclic terpenoids having a 1,1,5-trimethyl- trans -decalin nucleus: syntheses of (+)-acuminolide, (−)-spongianolide A, and (+)-scalarenedial
作者: Noriyuki FuruichiToshiyuki HataHartati SoetjiptoMariko KatoShigeo Katsumura
作者单位: 1School of Science, Kwansei Gakuin University, Uegahara 1-1-155, Nishinomiya 662-8501, Japan
刊名: Tetrahedron, 2001, Vol.57 (40), pp.8425-8442
来源数据库: Elsevier Journal
DOI: 10.1016/S0040-4020(01)00825-0
关键词: terpenes and terpenoiodsbiologically active compoundscommon synthetic strategy115-trimethyl- trans -decalin nucleus
原始语种摘要: Abstract(#br)We have developed a simple and practical method for providing enantiomerically pure bi-, tri-, and tetracyclic frameworks having a 1,1,5-trimethyl-trans-decalin nucleus, and demonstrated their utility for terpenoid synthesis. Thus, we achieved the stereocontrolled total syntheses of (+)-acuminolide as a bicyclic, (−)-spongianolide A as a tricyclic, and (+)-scalarenedial as a tetracyclic terpenoid from the corresponding optically pure cyclic β-ketoesters, which were obtained by repeating the same method of the ring construction, including the olefin cyclization with Lewis acid, followed by simple optical resolution using chiral auxiliaries for acetal formation, respectively. This is a general and valuable strategy for the synthesis of enantiomerically pure cyclic terpenoids...
全文获取路径: Elsevier  (合作)
影响因子:2.803 (2012)

  • trimethyl 三甲基
  • trans 会报
  • terpenoids 萜类
  • and 
  • tetracyclic 四轮列的
  • decalin 十氢化萘
  • strategy 战略
  • having 满足条件
  • nucleus 晶核
  • acetal 乙缩醛