Physical Sciences and Mathematics Commons^™

Synthesis Of Montiporynes A And B, Traci Jenelle Speed

Honors Theses

This thesis reports the first complete synthesis of monriporynes A and B. isomeric diacetylenes that bear α, β unsaturated ketone functionalities. Recently isolated from the stony coral Montipora sp. these compounds are reported to possess in vitro cytotoxic activity against several human solid tumor cells. We have synthesized both isomers in three simple steps. In the first step, l-iodononyne was prepared by reacting 1-nonyne with N-iodosuccinimide and a catalytic amount of silver nitrate. This iodoalkyne was then coupled with propargyl alcohol using copper iodide as the catalyst to give 2,4dodecadiynyl alcohol. Finally, the diacetylenic alcohol was subjected to the Swern …