Pinacol Coupling Strategy for the Construction of the Bicyclo[6.4.1]tridecane Framework of Schiglautone A
Bettina Werner1, Markus Kalesse1,2
1Institute for Organic Chemistry, Leibniz Universität Hannover , Schneiderberg 1B, D-30167 Hannover, Germany.
Abstract:
The synthesis of the tricyclic carbon framework of schiglautone A (1) is reported herein. The generation of the bicyclo[6.4.1]tridecane 19 was accomplished via a SmI2-mediated pinacol coupling of dialdehyde 18. The side chain in 18 was introduced using a selective 1,4-addition. A further key step of the synthesis was the homologation of a Wieland-Miescher ketone derivative to establish the 7-membered ring.
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