An efficient asymmetric synthesis of grenadamide

Reference:

Green, R., Cheeseman, M., Duffill, S., Merritt, A. and Bull, S. D., 2005. An efficient asymmetric synthesis of grenadamide. Tetrahedron Letters, 46 (46), pp. 7931-7934.

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Abstract

The cyclopropane containing natural product grenadamide has been prepared in six steps using (R)-5,5-dimethyl-oxazolidin-2-one as a chiral auxiliary for asymmetric synthesis. Key synthetic steps include the use of the P-hydroxyl group of a syn-aldol product as a 'temporary' stereocentre to control the facial selectivity of a directed cyclopropanation reaction, as well as the use of phenylethylamine as a nucleophile for the direct aminolysis of an N-acyl-oxazolidin-2-one intermediate. (c) 2005 Elsevier Ltd. All rights reserved.

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