喹诺里西啶类生物碱(-)-lasubine Ⅱ的全合成  

Total synthesis of quinolizidine alkaloids(-)-lasubine Ⅱ

作　　者：刘胜洋[1] 华维一[1] 阿吉艾克拜尔[2] 廖立新[2] 王伟[3] 

机构地区：[1]中国药科大学药物化学教研室,南京210009 [2]中国科学院上海药物研究所,上海201203 [3]新墨西哥大学化学系

出　　处：《中国药科大学学报》2007年第3期193-198,共6页Journal of China Pharmaceutical University

摘　　要：目的:研究喹诺里西啶类生物碱(-)-lasubineⅡ新的全合成路线并加以改进。方法:从简便易得的原料,通过两次高立体选择性的Roush硼烯丙基化反应以及SN2环合的方法构建3个手性中心,并利用关环复分解反应完成喹诺里西啶类生物碱(-)-lasubineⅡ的骨架构建。结果与结论:经13步反应,以15.3%的总收率完成了天然产物(-)-lasubineⅡ的全合成。经过测定,其1H NMR、EI-MS1、3C NMRI、R和旋光值与文献值相吻合。Aim： To study and improve enantioselective total synthesis of quinolizidine alkaloid （-）-lasubine Ⅱ. Methods： A new approach to total synthesis of （-）-lasubine Ⅱ was established from readily available starting materials, via the new synthetic sequence including the creation of stereogenic centers through two sequential highly stereoselective Roush allylborations, SN2 cyclization and ring-closing metathesis reactions for the construction of the lasubine＇s quinolizidine skeleton. Results and Conclusion： The synthesis of natural product （-）-lasubine Ⅱ has been accomplished by a new synthetic route in an overall yield of 15.3 % and its spectrum data, including ^1 H NMR, ^13 C NMR, EI-MS, IR and optical rotation, is in agreement with the literature data.

关 键 词：lasubine 喹诺里西啶 关环复分解反应 Roush不对称硼烷基化 

分 类 号：R914.5[医药卫生—药物化学]