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.File in questo prodotto:
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