Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (05): 653-659. Previous Articles     Next Articles

Original Articles

De Mayo光环加成和桥(螺)环倍半萜基本碳架的构建

王进军*,1,纪建业2,森章3   

  1. (1烟台大学应用化学系 烟台 264005)
    (2通化师范学院化学系 通化 134002)
    (3九州大学机能物质研究所 日本)
  • 收稿日期:2005-08-03 修回日期:2005-11-16 发布日期:2006-04-28
  • 通讯作者: 王进军

De Mayo Photocycloaddition and Construction of Basic Framework for Spiro- and Bridged-sesquiterpenes

WANG Jin-Jun*,1,JI Jian-Ye2,MORI Akira3   

  1. (1 Department of Applied Chemistry, Yantai University, Yantai 264005)
    (2 Department of Chemistry, Tonghua Teachers College, Tonghua 134002)
    (3 Institute of Advanced Material Study, Kyushu University, Japan)
  • Received:2005-08-03 Revised:2005-11-16 Published:2006-04-28
  • Contact: WANG Jin-Jun

The photocyclo-adducts, the opening products and radical recombination products 310 were obtained by de Mayo reaction of 3-isopropylidene-6-methylcyclohexene with methyl 2,4-dioxopentanoate. The photocyclo-adduct 3 was subjected to retro-aldol rearrangement to yield the substituted-cyclohexene 4. In acid or basic condition the recyclization of the opening product was carried out, and spirocyclic and bridged compounds 1114 were obtained by intramolecular Claisen condensation. The reaction mechanisms were discussed and the structures of all compounds were assigned based on the data derived from IR, 1H NMR 13C CMR and elemental analysis.

Key words: spirocyclic compound, bridged compound, Claisen condensation, photocycloaddition