Total synthesis of taspine and a symmetrical analogue: Study of binding to G-quadruplex DNA by ESI-MS

Taspine is an alkaloid found in the latex of certain trees belonging to the family of Euphorbiaceae, commonly called "Sangre de Drago" (Dragon's blood). Its structure and antineoplastic properties are well known. Here we report the total synthesis of taspine, starting from ferulic acid and isovanillin. The successful synthetic strategy was then applied to the synthesis of a symmetrical analogue TAS2C. Both the synthesised compounds were tested by ESI-MS (electrospray ionisation mass spectrometry) for their ability to bind different quadruplex and duplex DNA structures. We report the total synthesis of taspine and its symmetrical analogue TAS2C. Both the synthesised compounds were tested by ESI-MS for their ability to bind different quadruplex and duplex DNA structures. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim