|
|||||
|
|
Influence of ring fusion stereochemistry on the stereochemical outcome in photo-induced Diels–Alder reaction of fused bicycloheptenone derivatives |
|
| Institution: | 1. Multidisciplinary Science Research Center, National Sun Yat-Sen University, Kaohsiung 80424, Taiwan, ROC;2. Department of Physics, Center for Nanoscience and Nanotechnology, National Sun Yat-Sen University, Kaohsiung 80424, Taiwan, ROC;3. Department of Materials and Optoelectronic Science, National Sun Yat-Sen University, Kaohsiung 80424, Taiwan, ROC;4. United Crystal Corporation, No. 243-3, Wenshan 36061, Miaoli, Taiwan, ROC |
| Abstract: | Photo-isomerization of cis-cycloheptenone fused to a ring with a defined stereochemistry at the ring fusion to its trans-stereoisomer and in situ Diels–Alder reaction with cyclic and acyclic dienes have been investigated. The reaction was found to proceed through one of the two possible isomerized trans-enones that produce the thermodynamically more stable adduct with a trans-fused seven-membered ring system. This protocol has been employed to construct a tetracycle with trans-fused 6-7 ring system, the core structure present in several terpenes. The observed selectivity has been supported by computational method. |
| Keywords: | Photochemistry Isomerization Cycloaddition Terpenes |
| 本文献已被 ScienceDirect 等数据库收录！ | |