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ChemInform Abstract: Total Syntheses of the Strychnos Indole Alkaloids (-)-Tubifoline, (-)- Tubifolidine, and (-)-19,20-Dihydroakuammicine.

✍ Scribed by M. AMAT; M.-D. COLL; J. BOSCH; E. ESPINOSA; E. MOLINS

Publisher: John Wiley and Sons
Year: 2010
Weight: 34 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199731194

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✦ Synopsis

Total Syntheses of the Strychnos Indole Alkaloids (-)-Tubifoline, (-)-Tubifolidine, and (-)-19,20-Dihydroakuammicine. -The key steps in the synthesis of the title compounds (X), (XI), and ( XIII) are kinetic resolution of the racemic alcohol (I), orthoester Claisen rearrangement to the ester (IV), smith indolization of the ester (IV) and cyclization of the chloride (VII) and the amine (IX).

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