Highly Stereoselective Synthesis of trans -Dihydronarciclasine Analogues

Gábor Varró, Lenke Mattyasovszky, A. Grün, András Simon, L. Hegedûs, István Kádas

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Several new trans -dihydronarciclasine analogues were stereo selectively synthesised by applying our feasible and efficient process developed recently. These new phenanthridone alkaloid derivatives were obtained in both racemic and optically active forms. During their enantioselective syntheses, high selectivities (up to 99% ee) were achieved by using (8 S,9 S)-9-amino(9-deoxy)epiquinine as an organocatalyst. The modifications, the introduction of ethoxy or methoxy groups, were made in ring A of the phenanthridone scaffold.

Original languageEnglish
Article numberss-2017-t0559-op
Pages (from-to)625-643
Number of pages19
JournalSynthesis (Germany)
Volume50
Issue number3
DOIs
Publication statusPublished - Feb 1 2018

Fingerprint

Alkaloids
Scaffolds
Derivatives
dihydronarciclasine
phenanthridone

Keywords

  • alkaloids
  • organocatalysis
  • phenanthridone scaffold
  • stereoselective synthesis
  • trans -dihydronarciclasine analogues

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Varró, G., Mattyasovszky, L., Grün, A., Simon, A., Hegedûs, L., & Kádas, I. (2018). Highly Stereoselective Synthesis of trans -Dihydronarciclasine Analogues. Synthesis (Germany), 50(3), 625-643. [ss-2017-t0559-op]. https://doi.org/10.1055/s-0036-1591514

Highly Stereoselective Synthesis of trans -Dihydronarciclasine Analogues. / Varró, Gábor; Mattyasovszky, Lenke; Grün, A.; Simon, András; Hegedûs, L.; Kádas, István.

In: Synthesis (Germany), Vol. 50, No. 3, ss-2017-t0559-op, 01.02.2018, p. 625-643.

Research output: Contribution to journalArticle

Varró, G, Mattyasovszky, L, Grün, A, Simon, A, Hegedûs, L & Kádas, I 2018, 'Highly Stereoselective Synthesis of trans -Dihydronarciclasine Analogues', Synthesis (Germany), vol. 50, no. 3, ss-2017-t0559-op, pp. 625-643. https://doi.org/10.1055/s-0036-1591514
Varró, Gábor ; Mattyasovszky, Lenke ; Grün, A. ; Simon, András ; Hegedûs, L. ; Kádas, István. / Highly Stereoselective Synthesis of trans -Dihydronarciclasine Analogues. In: Synthesis (Germany). 2018 ; Vol. 50, No. 3. pp. 625-643.
@article{f92b9e4205b2490bb2d44a734d61c27d,
title = "Highly Stereoselective Synthesis of trans -Dihydronarciclasine Analogues",
abstract = "Several new trans -dihydronarciclasine analogues were stereo selectively synthesised by applying our feasible and efficient process developed recently. These new phenanthridone alkaloid derivatives were obtained in both racemic and optically active forms. During their enantioselective syntheses, high selectivities (up to 99{\%} ee) were achieved by using (8 S,9 S)-9-amino(9-deoxy)epiquinine as an organocatalyst. The modifications, the introduction of ethoxy or methoxy groups, were made in ring A of the phenanthridone scaffold.",
keywords = "alkaloids, organocatalysis, phenanthridone scaffold, stereoselective synthesis, trans -dihydronarciclasine analogues",
author = "G{\'a}bor Varr{\'o} and Lenke Mattyasovszky and A. Gr{\"u}n and Andr{\'a}s Simon and L. Heged{\^u}s and Istv{\'a}n K{\'a}das",
year = "2018",
month = "2",
day = "1",
doi = "10.1055/s-0036-1591514",
language = "English",
volume = "50",
pages = "625--643",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "3",

}

TY - JOUR

T1 - Highly Stereoselective Synthesis of trans -Dihydronarciclasine Analogues

AU - Varró, Gábor

AU - Mattyasovszky, Lenke

AU - Grün, A.

AU - Simon, András

AU - Hegedûs, L.

AU - Kádas, István

PY - 2018/2/1

Y1 - 2018/2/1

N2 - Several new trans -dihydronarciclasine analogues were stereo selectively synthesised by applying our feasible and efficient process developed recently. These new phenanthridone alkaloid derivatives were obtained in both racemic and optically active forms. During their enantioselective syntheses, high selectivities (up to 99% ee) were achieved by using (8 S,9 S)-9-amino(9-deoxy)epiquinine as an organocatalyst. The modifications, the introduction of ethoxy or methoxy groups, were made in ring A of the phenanthridone scaffold.

AB - Several new trans -dihydronarciclasine analogues were stereo selectively synthesised by applying our feasible and efficient process developed recently. These new phenanthridone alkaloid derivatives were obtained in both racemic and optically active forms. During their enantioselective syntheses, high selectivities (up to 99% ee) were achieved by using (8 S,9 S)-9-amino(9-deoxy)epiquinine as an organocatalyst. The modifications, the introduction of ethoxy or methoxy groups, were made in ring A of the phenanthridone scaffold.

KW - alkaloids

KW - organocatalysis

KW - phenanthridone scaffold

KW - stereoselective synthesis

KW - trans -dihydronarciclasine analogues

UR - http://www.scopus.com/inward/record.url?scp=85034752567&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85034752567&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1591514

DO - 10.1055/s-0036-1591514

M3 - Article

AN - SCOPUS:85034752567

VL - 50

SP - 625

EP - 643

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 3

M1 - ss-2017-t0559-op

ER -