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Pinacol Coupling Strategy for the Construction of the Bicyclo[6.4.1]tridecane Framework of Schiglautone A

Bettina Werner, Markus Kalesse

Org Lett. 2017 Apr 7;19(7):1524-1526.

PMID: 28300417

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP629505 Tridecane Tridecane 629-50-5 Price
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