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Journal of the Brazilian Chemical Society

On-line version ISSN 1678-4790

Abstract

FREDERICO, Daniel; CONSTANTINO, Mauricio G.  and  DONATE, Paulo M.. Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin. J. Braz. Chem. Soc. [online]. 2009, vol.20, n.5, pp. 888-894. ISSN 1678-4790.  http://dx.doi.org/10.1590/S0103-50532009000500013.

The total synthesis of enantiomerically enriched (3S, 5R, 3'S, 5'R)-capsorubin (1) by aldol condensation of (1R, 4S)-1-(4-hydroxy-1,2,2-trimethyl-cyclopentyl) ethanone (2a) and crocetindial (3) is described. An alternative, short eight-step synthesis of the optically active compound 2a (ee 89%) is also reported.

Keywords : carotenoid; capsorubin; crocetindial; cyclopentane keto-alkohol; synthesis.

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