Zsuzsanna Kardos-Balogh

A practical route to epibatidine

Abstract A practical synthetic approach to the alkaloid Epibatidine has been developed. This method is convenient and easy to scale up.

A PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF EPIBATIDINE

Abstract Two different syntheses of Epibatidine ( 1 ) were designed and carried out using easily accessible reagents and convenient reaction conditions. The ring closure of the prochiral precursor 4 catalyzed by optically active α-phenyl-ethyl-amine gave the key intermediate 5 in over 80% ee from which the natural product (−)- 1 has been prepared.

Synthesis of vinca alkaloids and related compounds. LXII: Synthesis of desmethoxy “decarbomethoxy apocuanzine”

Starting from the intermediate product (5) of the desmethoxy cuanzine synthesis, (±)-desmethoxy “decarbomethoxy apocuanzine” (4) was synthesized.

Synthesis of vinca alkaloids and related compounds LV synthesis of (±)-desmethoxy cuanzine

Abstract Through the key intermediate enamine ( 28 ) (±)-desmethoxy cuanzine ( 2 ) was synthesised.

SYNTHESIS OF VINCA ALKALOIDS AND RELATED COMPOUNDS. LXV: PREPARATION OF 7-METHOXYTRYPTAMINE

Abstract 7-Methoxytryptamine (6a) was prepared from cheap and easily available starting materials by using the Abramovitch-Shapiro method.

Synthesis of Vinca Alkaloids and Related Compounds, LXXI : Synthesis of (±)-cuanzine, (±)-decarbomethoxyapocuanzine, and some of their epimers

Abstract Starting from 7-methoxytryptamine (7) with the use of the method we developed earlier, (±)-cuanzine (1),(±)-decarbomethoxyapocuanzine (4), and their epimers 5 and 22 were synthesized.

Chapter 3 Epibatidine

Publisher Summary This chapter describes the occurrence, structure and synthesis, NMR spectroscopy, and pharmacology of epibatidine. Epibatidine is so far isolated only from the skin extract of an Ecuadorian poison frog of the family Dendrobatidae. The structure elucidation reveals that epibatidine has a 7-azabicyclo(2.2.l)heptene ring system containing a chloropyridyl substituent. The Diels-Alder reaction seems to be the most convergent method to construct the desired 7-azabicyclo(2.2. l)heptane ring system. The 7-azabicyclo(2.2. l)heptene ring system can also be constructed by an intramolecular nucleophilic substitution reaction. The trans position of the amino group or the protected amino group and the leaving group is the main prerequisite of ring closure. Epibatidine proves to be a 200 times more potent analgesic than morphine in the hot-plate and Straub-tail tests. Intriguingly, epibatidine seemed to operate via a nonopioid mechanism, because naloxone, a generally used opioid antagonist, did not reverse its effect.

Synthesis of vinca alkaloids and related compounds XXVII formation of a stable 3-acylindolenine☆

Abstract A stable 3-acylindolenine derivative (2) has been prepared via intramolecular electrophilic acylation. The reactivity of 2 has been studied.

Synthetic Studies in the Alkaloid Field

It is a common knowledge that plants are useful sources of many valuable medicines. Among these medicines several indole alkaloids can be found, e.g. reserpine and deserpidine from Rauwolfia serpentina, ajmalicine and yohimbine from Corynanthe yohimbe, vinblastine and vincristine from Cathavanthus roseus, just to mention a few of them.