Synthesis of (14R)- and (14S)-14-de(hydroxymethyl)-14-hydroxymycaminosyl tylonolides.
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The title compounds <B>29</B> and <B>19</B> have been prepared from mycaminosyl tylonolide 9,20-bis(ethylene acetal) via 9 (for <B>19</B>) and 13 steps (for <B>29</B>). The key step in the synthesis of <B>19</B> is Baeyer-Villiger reaction applied to 2′,4′-di-<I>O</I>-acetyl-3-<I>O</I>-<I>t</I>-butyldimethylsilyl-23-deoxy-23-oxomycaminosyl tylonolide 9,20-bis(ethylene acetal), and the desired 14-<I>O</I>-formyl derivative is obtained with other products including 12,13-epoxy and 14-<I>C</I>-carboxylic acid. The key step in the synthesis of <B>29</B> is Mitsunobu reaction applied to (14<I>S</I>)-2′,4′-di-<I>O</I>-acetyl-3-<I>O</I>-<I>t</I>-butyldimethylsilyl-14-de(hydroxymethyl)-14-hydroxymycaminosyl tylonolide 9,20-bis(ethylene acetal), and the desired (14<I>R</I>)-acyloxy product is obtained by inversion at C-14, with other compounds including 10(11), 12(22), 13(14)-triene and 12-acyloxy-10(11),13(14)-diene.
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