天然产物Trichodermamide类似物的合成

The Synthesis of the Analogue of Trichodermamide

摘要:

以8a-甲氧基-4,4a,5,8-四氢-1,2-苯并噁嗪-3-羧酸乙酯(1a)为起始原料，经NaOH醇溶液和酸化处理，再通过4-pyrrolidinopyridine催化、DCC脱水与3-氨基-7,8-二甲氧基香豆素（2）的酰胺化反应，首次成功合成了天然产物Trichodermamides的类似物T-1，总收率为61.6%，T-1通过了1HNMR, 13C-NMR，IR 和元素分析等光谱学的结构表证；同时水解反应研究发现，含苯并噁嗪双环结构的化合物1a可水解脱去酯基，而噁嗪双环8a位上连有两个O的缩酮类似结构可稳定地保留。

Abstract:

The first analogue of Trichodermamide T-1 was synthesized from 3-ethoxycarbonyl-8a- methoxy-4,4a,5,8-tetrahydro-1,2-benzoxazine (1a) in 61.6% by hydrolysis in alkaline alcohol solution and amidation reaction with amino-coumarin(2), subsequently. The structure of the compound T-1 was determined by 1HNMR, 13C-NMR，IR and elemental analysis. Investigation on the hydrolysis reaction showed that the bicyclic oxazine ester (1a) can be converted to the oxazine acid (1c) by losing the –OCH3 group. However, the double oxygen-bearing carbon structure of 8a on the oxazine ring can keep stable in the same condition.