A novel macroreticular-type fluorous polystyrene resin and its application to the synthesis of a 3-amino-beta-carboline derivative with N-methyl-N-nitrosourea conjugation via fluorous solid-phase reaction: a comparative study of fluorous solid-, solid-, and liquid-phase reactions

作者：Suzuki Keiko; Kumagai Munenori; Utsunomiya Masamichi; Sakai Norio; Konakahara Takeo^*

来源：Tetrahedron, 2015, 71(30): 4999-5012.

DOI：10.1016/j.tet.2015.05.072

• Fluorous polystyrene
• Fluorous synthesis
• Fluorous trityl chloride
• beta-carboline
• Nitrosourea
• Fluorous-solid phase reaction

A novel fluorous polystyrene (FPS) MR-resin was applied to a fluorous solid-phase (FSP) reaction. The MR-FPS resin actually was developed previously and possessed excellent chemical resistance to acids and alkalis, and a fluorous-tagged compound was homogeneously and loosely immobilized on the resin. The synthesis of an antitumor drug, an N-methyl-N-nirosourea conjugated 3-amino-beta-carboline derivative, was accomplished with a high yield by using this new fluorous reaction system. Using only filtration, the fluorous 3-amino-beta-carboline derivatives immobilized on the MR-FPS resin were easily recovered from the reaction mixtures. As an extention of this approach, a diversity synthesis of 3-amino-9-benzyl-beta-carboline derivatives was applied to the FSP method giving high yields. Finally, the FSP synthesis was compared with the corresponding conventional solid- and liquid-phase methods of synthesis. The FSP reaction was superior in terms of the reactivity of the substrate and the ease of product separation.

• 出版日期2015-7-29