R. Mitschka, J. Oehldrich, K. Takahashi
1981
Citations
0
Influential Citations
41
Citations
Journal
Tetrahedron
Abstract
Abstract The condensation of dimethyl 3-ketoglutarate 1 with 1,2-dicarbonyl compounds provides access to the polyquinane derivatives tricyclo[6.3.0.01,5] undecane - 3,7.9 - trione 27, tricyclo [3 3 3 01,5]undecane 31; tetra-cyclo [5.5.1.04,13.010,13] - tridecane - 2,6,8,12 - tetraone 41; tetracyclo[6.6.0.01,5. 08,12] tetradecane - 2,7,9,14 - tetraone 44, and the tetracyclo[5.5.1.010,13]tridecane triones 5b and 6b. The unique structure of staurane tetraone 41 has resulted in spontaneous resolution of the two antipodes on crystallization from DMF. In addition, examination of the crystal structures of tetraones 41 and 44, in terms of strain energy, coupled with the steric accessibility of the β-diketone functionality contained in 41 and 44 have been employed to explain why tetraone 44 and trione 27 undergo a retro-Claisen reaction (CH3OH) more rapidly than staurane tetraone 41.