Novel Zinc Mediated Indole Ring Opening of Isoreserpine

HETEROCYCLES
1999.0

Abstract

Reaction of reserpine'(1) with Zn/TFA resulted in isoreserpine (2), dihydro compound (7), and amino compound (8) via initial epimerization at C- 3. The latter two compounds constitute a novelty in indole alkaloid chemistry: the dihydro compound (7) possesses unusual H-2/H-7 cis and H-2/H-3 trans relationships, whereas the amino compound (8) displays a novel zinc mediated indole ring scission.

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