Synthesis of Marine Synomone "Aplysinopsin" Related Compounds

点击翻译按钮获取中文摘要

In order to synthesize the related compound of antitumor marine synomon "Aplysinopin", the reactins of 3,5-bis(methoxycarbonyl)-2-isoxazoline-2-oxide derivatioves with titanium tetrachloride were investigated as follows :1. The reaction of 4-(m-substituted phenyl)-3,5-bis(methoxycarbonyl)-2-isoxazoline-2-oxides with titanium tetrachloride did not afford desired 3H-indole-1-oxides, but alpha-hydroxy-4H-1,2-benzoxazines were isolated.The latter compunds were converted to 2-oxo-2H-benzofuro[2,3-b]pyrroles in a thre step sequence.2.4-(p-Substituted phenyl)-3,5-bis(methoxycarbonyl)-2-isoxazoline-2-oxides were reacted with titanium tetrachlride to afford benzofuro[3,3a-d]-isoxazoles and their Diels-Alder dimers.3.5-Hydroxymethyl-3-methoxycarbonyl-4-(p-substituted phenyl)-2-isoxazoline-2-oxides converted to benzofuro[2,3-c]tetrahydrofurans and benzofuro-[3,2-d]-1,2-oxazines by the action of titanium tetrachloride.4. The reaction of 4-indolyl-3,5-bis(methoxycarbonyl)-2-isoxazoline-2-oxide with titanium tetrachloride yielded desired alpha-hydroxyindo[2,3-b]-1-pyrrole-1-oxiede, which can be the synthetic precursor of the related comound of antitumor marine synomone "Aplysinopusin".