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Studies on the synthesis of Strychnos indole alkaloids

✍ Scribed by Joan Bosch; Marisa Salas; Mercedes Amat; Mercedes Alvarez; Isabel Morgó; Bartomeu Adrover

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
738 KB
Volume
47
Category
Article
ISSN
0040-4020

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✦ Synopsis

Tetracycles 3b-d, having the ABCD ring substructure of Strychnos alkaIoids and a &(formvhnethvl) substituent mokcted as an oxime or hvdraxone derivative. have been p&&d-by nu&phiIic addition of the enolate of indok.a&tic ester 1 to pyridinium salts 2b-d followed by acid cyclization. The same one-pot, two-step sequence allowed the preparation of tetracycle 3f. which incorporates an a-methoxyacrylate chain at the piperidine $-position. We have recently developed a new strategy for the synthesis of pentacyclic Strychnos alkaloids.1*2 It consists in the closure of the five-membered E ring by electrophilic cyclixation upon the indole 3-position from appropriate tetracyclic derivatives (the ABCD substructure of Srrychms alkaloids) having a functionalixed two-carbon chain at the piperldhte nitrogen (bond formed C&)? qg-gRs_& Rl I h R2

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