Polyene cyclization promoted by the cross-conjugated alpha-carbalkoxy cyclohexenone system. An unusual 1,2-hydride shift under Lewis acid catalysis.
Polyene cyclization of the titled compounds under catalysis with AlCl(3)/SnCl(4) gave rise to the corresponding polycyclic products, many of which were structurally highly unexpected, and thus, individual X-ray analysis was required to finalize the structural identification. Mechanistically, an unusual 1,2-hydride shift is proposed to elucidate the product formation.
Hsieh
Min-Tsang
MT
Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Miaoli County 350, Taiwan, ROC.
Chou
Ho-Hsuan
HH
Liu
Hsing-Jang
HJ
Wu
Huang-Min
HM
Ly
Tai Wei
TW
Wu
Yen-Ku
YK
D000077410:Aluminum Chloride; D017607:Aluminum Compounds / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011090:Polyenes / Q000737:chemistry*; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry
D017607:Aluminum Compounds; D002712:Chlorides; D003512:Cyclohexanones; D011083:Polycyclic Compounds; D011090:Polyenes; D017971:Tin Compounds; C023599:stannous chloride; D000077410:Aluminum Chloride