Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 51, No. 12, 1999, pp.2941-2948
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8718
Novel Zinc Mediated Indole Ring Opening of Isoreserpine

Mathias Berner, Arto Tolvanen, Mauri Lounasmaa,* and Reija Jokela*

*Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki, P.O. Box 6100, FIN-02150 HUT Espoo, Finland

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.