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Piperidine dispiro-1,2,4-trioxane analogues.

Bioorganic & medicinal chemistry letters (2008-10-11)
Sunil Sabbani, Paul A Stocks, Gemma L Ellis, Jill Davies, Erik Hedenstrom, Stephen A Ward, Paul M O'Neill
ABSTRACT

Dispiro N-Boc-protected 1,2,4-trioxane 2 was synthesised via Mo(acac)(2) catalysed perhydrolysis of N-Boc spirooxirane followed by condensation of the resulting beta-hydroperoxy alcohol 10 with 2-adamantanone. N-Boc 1,2,4-trioxane 2 was converted to the amine 1,2,4-trioxane hydrochloride salt 3 which was subsequently used to prepare derivatives (4-7). Several of these novel 1,2,4-trioxanes had nanomolar antimalarial activity versus the 3D7 strain of Plasmodium falciparum. Amine intermediate 3 represents a versatile derivative for the preparation of achiral arrays of trioxane analogues with antimalarial activity.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2-Adamantanone, ReagentPlus®, 99%