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Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin

DOI: 10.1590/S0103-50532009000500013

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

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Abstract:

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.

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