New solutions to the C-12,13 stereo-problem of epothilones B and D; synthesis of a 12,13-diol-acetonide epothilone B analog
Gaich, Tanja; Karig, Gunter; Martin, Harry J.; Mulzer, Johann.
European Journal of Organic Chemistry (2006), (15), 3372-3394.
New approaches are described to the synthesis of epothilone B and a 12,13-diol-acetonide derivative. Specifically the (12Z) double bond is formed quantitatively by a silicon-tethered ring-closing metathesis (RCM) reaction with 85 % selectivity. Alternatively, a direct route to the 12,13-epoxide by cyclization of a 12,13-diol has been developed.
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Johann Mulzer
Institute for Organic Chemistry
University of Vienna
Währingerstraße 38
A-1090 Vienna
Institute for Organic Chemistry
University of Vienna
Währingerstraße 38
A-1090 Vienna