New Domino Silyl Enol Ether Reactions in the Synthesis of a Tetrodecamycin Fragment

Abstract

AbstractOn 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 sequence. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)