摘要
目的改进多烯紫杉醇的合成工艺,寻找一条适合于工业生产的切实可行的合成路线。方法以顺式肉桂酸乙酯为起始原料,经不对称环氧化、叠氮开环、氢化等反应制备唑烷羧酸型侧链;将该侧链与选择性保护的母核结构—10-去乙酰基巴卡亭Ⅲ连接,经酯化、脱保护基反应合成多烯紫杉醇。结果目标化合物的结构经1H-NMR、13C-NMR、MS、IR、元素分析确证,合成C13位手性侧链的收率为66%,酯化及脱保护反应的收率为60%。结论新工艺路线采用低成本原料,简单可行,适合于工业化生产。
Aim To improve the synthetic procedure of daxotere and to develop a simple and economic method to synthesize daxotere.Methods With cis-ethyl cinnamate as starting material,the chiral oxazolidine carboxylic acid daxotere C13 side chain was synthesized via asymmetric epoxidation,diazotization and hydrogenation,etc.Then it was coupled with selective protected 10-deacetylbaccatin Ⅲ via esterification,followed by deprotection to afford daxotere.Results The product was characterized by elemental analysis,IR,NMR,MS,etc.Chiral daxotere C13 chain was synthesized in 66% yield.The total yield of esterification and deprotection was 60%.Conclusion The new synthetic route is simple,economic and might be benefit for industrialization.
出处
《中国药物化学杂志》
CAS
CSCD
2009年第5期356-360,共5页
Chinese Journal of Medicinal Chemistry
