Ramage R
Ciba Found Symp. 1978(53):67-83. doi: 10.1002/9780470720349.ch6.
The contribuation made by Sir Robert Robinson to sesquiterpene chemistry and to the development of the biogenetic isoprene rule are discussed. Examaples of the great utility of the Robinson Ring Annelation in synthetic organic chemistry are given with reference to steroid and sesquiterpene systems. Recent modifications to the original method are also mentioned. The close relationship of the eremophilane sesquiterpenes and the spiro sesquiterpenes, which follows from the biogenetic derivation of eremophilone by Robinson, is the basis for the synthetic strategy under discussion leading to chiral spiro sesquiterpenes. This approach makes use of chiral starting material couples with subsequent stereospecific processes leading to sesquiterpenes of stereochemical interest and complexity.
讨论了罗伯特·罗宾逊爵士对倍半萜化学以及生源异戊二烯规则发展所做的贡献。结合甾体和倍半萜体系,给出了罗宾逊环合反应在合成有机化学中巨大实用性的例子。还提到了对原始方法的近期改进。从罗宾逊对雅槛蓝酮的生源推导可以看出,雅槛蓝烷倍半萜和螺环倍半萜之间的密切关系,是所讨论的导致手性螺环倍半萜的合成策略的基础。这种方法利用手性起始原料,结合随后的立体专一性过程,得到具有立体化学意义和复杂性的倍半萜。