A chiral synthesis of (−)-cannabisativine: an application of the highly diastereo-selective hetero Diels-Alder reaction
作者:Tatsuo Hamada、Tatsuya Zenkoh、Hiroki Sato、Osamu Yonemitsu
DOI:10.1016/s0040-4039(00)74295-x
日期:1991.3
The polyamine alkaloid cannabisativine was synthesized as an optical active form. The key step is the hetero Diels-Alder reaction of chiral diene and an N-tosylimine, in which regio- and diastereo-face selectivities were completely controlled, only one diastereomer was isolated in high yield. Synthesized (−)-cannabisativine has the same physical data as the natural product except for the αD value.
合成多胺生物碱大麻脂为光学活性形式。关键步骤是手性二烯与N-甲苯磺胺的杂Diels-Alder反应,其中区域和非对映异构体的选择性得到完全控制,仅高产率地分离出一个非对映异构体。除了αD值外,合成的(-)-大麻二酚具有与天然产物相同的物理数据。