手性7-氨基脱氢枞酸乙酯的合成及表征

Synthesis and Characterization of Chiral Ethyl 7-Amino-Dehydroabietate

基于7-氨基脱氢枞酸衍生物在药物开发、手性催化和特殊光学材料等方面的潜在应用,该文以脱氢枞酸为起始原料,通过酯化、氧化、手性辅剂亚胺化、还原以及酸解脱除手性辅剂等反应获得光学纯的7-(S)-氨基脱氢枞酸乙酯Ⅵ和7-(R)-氨基脱氢枞酸乙酯Ⅷ,总产率分别为24.3%和8.7%。产物结构通过1HNMR、13CNMR、MS和HRMS进行表征,绝对构型经X-ray单晶衍射确定。

Based on the potential applications of 7-amino dehydroabietic acid derivatives in drug development,chiral catalysis, special optical materials, etc. , starting from dehydroabietic acid, optical pure ethyl 7-（ S ）-amino-dehydroabietate Ⅵ and ethyl 7-（ R）-amino-dehydroabietate Ⅷ were synthesized by esterification, oxidation, chiral auxiliary imidization, reduction and releasing the chiral auxiliary, in which the total yields of WI and VIII were 24.3 % and 8.7 % , respectively. The absolute configurations of the final products were confirmed by single crystal X-ray diffraction, and their structures were characterized by means of ^1HNMR, ^13CNMR, MS and HRMS.