New domino silyl enol ether reactions in the synthesis of a tetrodecamycin fragment

J He, K Tchabanenko, RM Adlington…

Index: He, Jing; Tchabanenko, Kirill; Adlington, Robert M.; Cowley, Andrew R.; Baldwin, Jack E. European Journal of Organic Chemistry, 2006 , # 17 p. 4003 - 4013

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Citation Number: 7

Abstract

Abstract On heating in toluene at 180 C for four days the TMS enol ether 7 underwent a domino acid catalysed rearrangement, Diels–Alder cycloaddition and further rearrangement to give the bicyclic TMS enol ether 17, which was converted into a tetrodecamycin precursor 3 in three synthetic steps. Further, monocyclic silyl enol ethers were consecutively treated with mCPBA and bromine to give syn α-hydroxy α′-bromo ketones in a one-pot reaction ...