Synthesis, x-ray crystal structure, and antimitotic properties of 6-chloro-2-methoxy-5-(2', 3', 4'-trimethoxyphenyl) cyclohepta-2, 4, 6-trien-1-one, a bicyclic analog of …

MG Banwell, KA Herbert, JR Buckleton…

Index: Banwell; Herbert; Buckleton; Clark; Rickard; Lin; Hamel Journal of Organic Chemistry, 1988 , vol. 53, # 21 p. 4945 - 4952

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Citation Number: 19

Abstract

A regiocontrolled synthesis of the bicyclic colchicine analogue 2 has been achieved. Thus, the readily available cyclohexenone 10 was elaborated to the tricyclic compounds 15a, 16b, and 17b, which were converted into the a-methoxy enone 6. Reaction of 6 with 1, 8- diazabicyclo [5.4. 0] undec-7-ene gave the title compound (2). Subjection of diol 17b to a Swern reaction, using excess oxidant, afforded the free tropolone 22, which, on 0- ...

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