A synthetic approach based on a palladium-mediated vinylation of indole derivatives was established for the preparation of 5, a key intermediate in the synthesis of N-(tert-butoxycarbonyl)-L-1H-[(R)-1,1-dimethyl-2,3-epoxypropyl]-beta-hydroxytryptophan ethyl ester (6). Unsatisfying yields were obtained using N-alkyl-3-haloderivatives. The best method proved to be the oxidative coupling on 3-unsubstituted indole derivative.

A Pd-Mediated Approach to the Synthesis of an Unusual beta-Hydroxytryptophan Amino Acid Constituent of Cyclomarin A.

DELLA SALA, Giorgio;IZZO, Irene;SPINELLA, Aldo
2006-01-01

Abstract

A synthetic approach based on a palladium-mediated vinylation of indole derivatives was established for the preparation of 5, a key intermediate in the synthesis of N-(tert-butoxycarbonyl)-L-1H-[(R)-1,1-dimethyl-2,3-epoxypropyl]-beta-hydroxytryptophan ethyl ester (6). Unsatisfying yields were obtained using N-alkyl-3-haloderivatives. The best method proved to be the oxidative coupling on 3-unsubstituted indole derivative.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/1539762
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