内分子DIELS-ALDER反应合成DRIMANE类倍半萜化合物DRIMENIN, POLYGODIAL及CINNAMOLIDE的全合成

近年来有不少报道从事于生理活性Drimane类倍半萜的合成,较多采用了分子间Diels-Alder反应来建立Drimane的骨架。本文首次采用内分子Diels-Alder反应作为关键反应合成了Drimane类化合物。同时还在引入了手性诱导基团后,首次完成了从无手性的原料化合物β-紫罗兰酮至光学活性(-)-drimenin1的不对称合成。

The Intramolecular Diels-Alder Approach to Drimane Related Sesquiterpenes Synthesis of Drimenin, Polygolyodial and Cinnamolde

Recently there has been increasing interest in the synthesis of biologically active sesqui- terpenes associated with drimane. Among a number of different synthetic strategies leading to these molecules, the application of the Diels-Alder reaction to construct an appropriately func- tionalised decalin is especially attractive. Up to now, there are quite a number of reports on the synthesis of drimane sesquiterpenes using the Diels-Alder reaction. However, to con- struct a decalin system using an intramolecular Diels-Alder reaction has not yet been explored. Here we report the synthesis of racemic and optically active drimane sesquiterpenes with the intramolecular Diels-Alder reaction as the key step.