Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1615-1626.DOI: 10.6023/cjoc201504031 Previous Articles     Next Articles



艾文英a, 廖道红a, 雷晓光b   

  1. a 天津大学药物科学与技术学院 天津 300072;
    b 北京大学化学与分子工程学院 化学生物学系 北京 100871
  • 收稿日期:2015-04-21 修回日期:2015-05-08 发布日期:2015-05-15
  • 通讯作者: 雷晓光
  • 基金资助:

    国家自然科学基金(Nos. 21472010, 91313303, 21222209)资助项目.

Applications of ortho-Quinone Methides in the Synthesis of Natural Products

Ai Wenyinga, Liao Daohonga, Lei Xiaoguangb   

  1. a School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072;
    b Department of Chemical Biology, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871
  • Received:2015-04-21 Revised:2015-05-08 Published:2015-05-15
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21472010, 91313303, 21222209).

ortho-Methylene cyclohexadienones, which are collectivelly referred to as ortho-quinone methides (o-QMs), were first suggested by Fries in 1907. o-QMs are a kind of short-lived and highly reactive versatile intermediates in organic synthesis. The unstability nature of o-QMs is due to their propensity to undergo rapid rearomatisation either by Michael addition of nucleophiles or, often more usefully, by cycloaddition with 2π partners or via oxa-6π-electrocyclisation to give benzopyrans. ortho-Quinone methides were always used in the synthesis of natural products through Michael addition and cycloaddition. As a new member of the family of inherently reactive species, ortho-quinone methides are similar with radicals, carbocations, carbenes, etc. And now using o-QMs to form skeletons of natural products has become a very useful stratergy. This review contains the major application in the synthesis of natural products during 2009 to 2014.

Key words: ortho-quinone methide, natural products, organic synthesis