Synthesis of carbocyclic hydantocidins via regioselective and diastereoselective phosphine-catalyzed [3+2]-cycloadditions to 5-methylenehydantoins

Authors

Tien Quoc Pham, University of Wollongong
Stephen G. Pyne, University of WollongongFollow
Brian W. Skelton, University of Western Australia
Allan H. White, University of Western Australia

RIS ID

12766

Publication Details

Pham, T., Pyne, S. G., Skelton, B. W. & White, A. H. (2005). Synthesis of carbocyclic hydantocidins via regioselective and diastereoselective phosphine-catalyzed [3+2]-cycloadditions to 5-methylenehydantoins. The Journal of Organic Chemistry, 70 (16), 6369-6377.

Abstract

The phosphine-catalysed [3+2]-cycloaddition of 5-methylenehydantoins 4 with the ylides 5, derived from addition of tributylphosphine to the 2-butynoic acid derivatives, 6a-d, gives spiro-heterocyclic products. The camphor sultam derivative 6b gives optically active products. Noteable was that the ylides derived from ethyl 2-butynoate and the 3-(2-butynoyl)-1,3-oxazolidin-2-one derivatives 6c and 6d gave spiro-heterocyclic products with reverse regioselectivities. The N,N-dibenzylprotected cycloadduct has been converted to carbocyclic hydantocidin and 6,7-diepi-carbocyclic hydantocidin.