Construction of the bicyclo[3.3.1]nonenone core by successive Michael reactions of 2-cyclohexenone derivatives

Tetrahedron Letters

Volumn 45, Issue 40, 2004, Pages 7401-7405

  Takagi, Ryukichi ^a   Nerio, Takashi ^a   Miwa, Yukiko ^a   Matsumura, Shuji ^a   Ohkata, Katsuo ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Bicyclo 3.3.1 nonenone; One pot reaction; Successive Michael reaction

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; ACRYLIC ACID DERIVATIVE; BICYCLO COMPOUND; BICYCLO[3.3.1]NONENONE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL STRUCTURE; MICHAEL ADDITION;

EID: 4444353704     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.068     Document Type: Article

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34. 4, filtered, and evaporated. The resulting residue was purified by preparative TLC (silica gel, hexane/EtOAc = 10/1) to give annulation products 4c and 5c (4c: 71%, 5c: 8%, Table 1, entry 6)
35. 1H NMR of 14a-c and 15a-c. The long range couplings indicate the preferred conformer of six-membered ring in the bicyclo[3.3.1]nonenone core
36. 3: C, 71.97; H, 8.86. Found: C, 72.02; H, 8.88
37. 4, filtered, and evaporated. The resulting residue was purified by preparative TLC (silica gel, hexane/EtOAc = 10/1) to give annulation products 14c, 15c and 16c (14c: 34%, 15c: 32%, 16c: 4%, Table 4, entry 3)