Synthetic studies towards paspalicine (cas 11024-55-8): Preliminary investigations, and the synthesis of 3′,4′,7′,7′a,9′,10′,11′,11′a-octahydro-4′,4′,7′a-trimethylspiro[1,3-dioxolane]-2,8′(6′H)-2′H-3′,5′a-epoxynaphth [2,1-b]oxepin-2′-one

Add time:08/18/2019    Source:sciencedirect.com

Preliminary investigations directed towards the synthesis of the indole-diterpene mould metabolite, paspalicine 1, are described. Following the preparation of the β-pyrone ketal 7, which contains the characteristic functional group of paspalicine, the compound 25, which constitutes rings D–G of paspalicine with the correct relative stereochemistry, has been synthesised in eight steps from the monoketal 12 of the Wieland-Miescher ketone, in an overall yield of 8%.

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