(4E,8E)-(1R,12R,13S,14S)-14-Benzyloxy-4,8,12-trimethyl-15-methylene-bicyclo[10.2.2]hexadeca-4,8-dien-13-ol | 134237-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4E,8E)-(1R,12R,13S,14S)-14-Benzyloxy-4,8,12-trimethyl-15-methylene-bicyclo[10.2.2]hexadeca-4,8-dien-13-ol
• CAS: 134237-93-7
• 化学式: C₂₇H₃₈O₂
• 分子量: 394.598
• InChiKey: CUBLJOKKMKBLGZ-IRMBACGTSA-N

反应信息

• 作为产物：
  描述：

  benzyl (1RS,2SR,3SR,6E,10E,14SR)-2,3-epoxy-14-(2-propenyl)-3,7,11-trimethyl-6,10-cyclotetradecadien-1-yl ether 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以20%的产率得到(4E,8E)-(1R,12R,13S,14S)-14-Benzyloxy-4,8,12-trimethyl-15-methylene-bicyclo[10.2.2]hexadeca-4,8-dien-13-ol
  参考文献：
  名称：

  Cyclization of polyenes. 49. Cyclization of epoxyneocembrene derivatives to secotrinervitanes

  摘要：

  Four stereoisomers of epoxyneocembrene derivatives 5-8 were treated with BF3.OEt2 as potential model reactions for the proposed biogenesis of secotrinervitane-type diterpenoids (Scheme I). Two of them (5 and 6) afforded secotrinervitane derivatives, while the remaining isomers 7 and 8 gave no cyclization products (Table I). The natural product, secotrinervitene-2-beta,3-alpha-diol (2a) was synthesized from 5 in dl-form.

  DOI：

  10.1021/jo00014a036