Synthesis of vinca alkaloids and related compounds, Part LXXXIX. Some unexpected reactions of compounds containing the D-seco-aspidospermane ring system

György Kalaus, Imre Juhász, Kinga Steinhauser, István Greiner, M. Kajtár-Peredy, János Brlik, Lajos Szabó, Csaba Szántay

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Interaction of the tryptamine derivative (3) with the formyl ester (4) gave (±)-20-deethyl-2,16-didehydro-14,16-bis(methoxycarbonyl)-3-phenyl-3,14- seco-20-epiaspidospermidine (7) instead of the expected acetal (6). The product of the reaction of 3 with the acetoacetic aldehyde derivative (5) was ethylene acetal of (±)-2,16-didehydro-16-methoxycarbonyl-3-phenyl-14,15- dinoraspidospermidin-19-one (8), it was readily convertible into the reactive intermediate (10). Further build-up starting from secondary amine (11) gave the N(4)-substituted derivatives, while 10 afforded products with unexpected structures. The reaction of 10 with acetic anhydride yielded different products depending on the reaction conditions.

Original languageEnglish
Pages (from-to)205-219
Number of pages15
JournalHeterocycles
Volume47
Issue number1
Publication statusPublished - 1998

Fingerprint

Vinca Alkaloids
Acetals
Derivatives
Aldehydes
Amines
Esters
tryptamine
ethylene
acetic anhydride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of vinca alkaloids and related compounds, Part LXXXIX. Some unexpected reactions of compounds containing the D-seco-aspidospermane ring system. / Kalaus, György; Juhász, Imre; Steinhauser, Kinga; Greiner, István; Kajtár-Peredy, M.; Brlik, János; Szabó, Lajos; Szántay, Csaba.

In: Heterocycles, Vol. 47, No. 1, 1998, p. 205-219.

Research output: Contribution to journalArticle

Kalaus, G, Juhász, I, Steinhauser, K, Greiner, I, Kajtár-Peredy, M, Brlik, J, Szabó, L & Szántay, C 1998, 'Synthesis of vinca alkaloids and related compounds, Part LXXXIX. Some unexpected reactions of compounds containing the D-seco-aspidospermane ring system', Heterocycles, vol. 47, no. 1, pp. 205-219.
Kalaus, György ; Juhász, Imre ; Steinhauser, Kinga ; Greiner, István ; Kajtár-Peredy, M. ; Brlik, János ; Szabó, Lajos ; Szántay, Csaba. / Synthesis of vinca alkaloids and related compounds, Part LXXXIX. Some unexpected reactions of compounds containing the D-seco-aspidospermane ring system. In: Heterocycles. 1998 ; Vol. 47, No. 1. pp. 205-219.
@article{dcab2a5805e247de89f745007b60d023,
title = "Synthesis of vinca alkaloids and related compounds, Part LXXXIX. Some unexpected reactions of compounds containing the D-seco-aspidospermane ring system",
abstract = "Interaction of the tryptamine derivative (3) with the formyl ester (4) gave (±)-20-deethyl-2,16-didehydro-14,16-bis(methoxycarbonyl)-3-phenyl-3,14- seco-20-epiaspidospermidine (7) instead of the expected acetal (6). The product of the reaction of 3 with the acetoacetic aldehyde derivative (5) was ethylene acetal of (±)-2,16-didehydro-16-methoxycarbonyl-3-phenyl-14,15- dinoraspidospermidin-19-one (8), it was readily convertible into the reactive intermediate (10). Further build-up starting from secondary amine (11) gave the N(4)-substituted derivatives, while 10 afforded products with unexpected structures. The reaction of 10 with acetic anhydride yielded different products depending on the reaction conditions.",
author = "Gy{\"o}rgy Kalaus and Imre Juh{\'a}sz and Kinga Steinhauser and Istv{\'a}n Greiner and M. Kajt{\'a}r-Peredy and J{\'a}nos Brlik and Lajos Szab{\'o} and Csaba Sz{\'a}ntay",
year = "1998",
language = "English",
volume = "47",
pages = "205--219",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "1",

}

TY - JOUR

T1 - Synthesis of vinca alkaloids and related compounds, Part LXXXIX. Some unexpected reactions of compounds containing the D-seco-aspidospermane ring system

AU - Kalaus, György

AU - Juhász, Imre

AU - Steinhauser, Kinga

AU - Greiner, István

AU - Kajtár-Peredy, M.

AU - Brlik, János

AU - Szabó, Lajos

AU - Szántay, Csaba

PY - 1998

Y1 - 1998

N2 - Interaction of the tryptamine derivative (3) with the formyl ester (4) gave (±)-20-deethyl-2,16-didehydro-14,16-bis(methoxycarbonyl)-3-phenyl-3,14- seco-20-epiaspidospermidine (7) instead of the expected acetal (6). The product of the reaction of 3 with the acetoacetic aldehyde derivative (5) was ethylene acetal of (±)-2,16-didehydro-16-methoxycarbonyl-3-phenyl-14,15- dinoraspidospermidin-19-one (8), it was readily convertible into the reactive intermediate (10). Further build-up starting from secondary amine (11) gave the N(4)-substituted derivatives, while 10 afforded products with unexpected structures. The reaction of 10 with acetic anhydride yielded different products depending on the reaction conditions.

AB - Interaction of the tryptamine derivative (3) with the formyl ester (4) gave (±)-20-deethyl-2,16-didehydro-14,16-bis(methoxycarbonyl)-3-phenyl-3,14- seco-20-epiaspidospermidine (7) instead of the expected acetal (6). The product of the reaction of 3 with the acetoacetic aldehyde derivative (5) was ethylene acetal of (±)-2,16-didehydro-16-methoxycarbonyl-3-phenyl-14,15- dinoraspidospermidin-19-one (8), it was readily convertible into the reactive intermediate (10). Further build-up starting from secondary amine (11) gave the N(4)-substituted derivatives, while 10 afforded products with unexpected structures. The reaction of 10 with acetic anhydride yielded different products depending on the reaction conditions.

UR - http://www.scopus.com/inward/record.url?scp=0011201984&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0011201984&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0011201984

VL - 47

SP - 205

EP - 219

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 1

ER -