The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16'-epi-Leucophyllidine.

Azabicyclo Compounds / chemical synthesis Indole Alkaloids / chemical synthesis Molecular Structure Stereoisomerism Vinca Alkaloids / chemical synthesis
alkaloids convergence cross-coupling divergence total synthesis

Journal

Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543

Informations de publication

Date de publication:
09 08 2021
Historique:
received: 07 05 2021
pubmed: 27 5 2021
medline: 3 11 2021
entrez: 26 5 2021
Statut: ppublish

Résumé

A synthetic approach to the heterodimeric bisindole alkaloid leucophyllidine is disclosed herein. An enantioenriched lactam building block, synthesized through palladium-catalyzed asymmetric allylic alkylation, served as the precursor to both hemispheres. The eburnamonine-derived fragment was synthesized through a Bischler-Napieralski/hydrogenation approach, while the eucophylline-derived fragment was synthesized by Friedländer quinoline synthesis and two sequential C-H functionalization steps. A convergent Stille coupling and phenol-directed hydrogenation united the two monomeric fragments to afford 16'-epi-leucophyllidine in 21 steps from commercial material.

Identifiants

DOI: 10.1002/anie.202106184 PMID: 34036708 PMC: PMC8338904
pubmed: 34036708
doi: 10.1002/anie.202106184
pmc: PMC8338904
mid: NIHMS1709884
doi:

Substances chimiques

Azabicyclo Compounds 0
Indole Alkaloids 0
Vinca Alkaloids 0
eucophylline 0
leucophyllidine 0
eburnamonine NPD9S131ZU

Types de publication

Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.

Langues

eng

Sous-ensembles de citation

IM

Pagination

17957-17962

Subventions

Organisme : NIGMS NIH HHS
ID : R01 GM080269
Pays : United States

Informations de copyright

© 2021 Wiley-VCH GmbH.

Références

J Org Chem. 2011 Jul 1;76(13):5198-206
pubmed: 21630712
Angew Chem Int Ed Engl. 2013 Oct 18;52(43):11257-60
pubmed: 24039135
Nat Chem. 2011 Dec 18;4(2):130-3
pubmed: 22270628
Chem Commun (Camb). 2008 Jul 7;(25):2873-5
pubmed: 18566709
J Am Chem Soc. 1968 Jul 31;90(16):4504-5
pubmed: 5666353
J Am Chem Soc. 2019 Mar 27;141(12):4811-4814
pubmed: 30848892
Org Lett. 2012 Dec 21;14(24):6166-9
pubmed: 23214465
Bioorg Med Chem Lett. 2010 Nov 15;20(22):6408-10
pubmed: 20932748
Org Lett. 2005 Sep 1;7(18):3881-4
pubmed: 16119922
Org Lett. 2011 Apr 1;13(7):1881-3
pubmed: 21384895
J Am Chem Soc. 2016 Oct 12;138(40):13179-13182
pubmed: 27670712
Planta Med. 1997 Apr;63(2):97-101
pubmed: 9140219
Org Lett. 2015 Sep 18;17(18):4518-21
pubmed: 26348122
J Org Chem. 2016 Aug 19;81(16):6980-7
pubmed: 27315015
J Am Chem Soc. 2016 Dec 7;138(48):15555-15558
pubmed: 27934032
Chem Rev. 2018 Apr 11;118(7):3752-3832
pubmed: 29516724
ACS Med Chem Lett. 2011 Dec 8;2(12):948-952
pubmed: 22247789
J Org Chem. 2001 Dec 28;66(26):8935-43
pubmed: 11749625
J Am Chem Soc. 1965 Apr 5;87:1580-9
pubmed: 14306194
J Org Chem. 2000 Aug 25;65(17):5433-5
pubmed: 10993380
Adv Synth Catal. 2015 Jul 6;357(10):2238-2245
pubmed: 27042171
Org Lett. 2017 Jun 16;19(12):3267-3270
pubmed: 28571324
J Org Chem. 1997 Apr 18;62(8):2312-2313
pubmed: 11671553
J Am Chem Soc. 2014 Jan 22;136(3):890-3
pubmed: 24410719
Planta Med. 1999 Dec;65(8):690-4
pubmed: 10630106
Angew Chem Int Ed Engl. 2017 Oct 2;56(41):12624-12627
pubmed: 28872739
Org Lett. 2009 Sep 3;11(17):3962-5
pubmed: 19708704
Curr Med Chem. 2006;13(2):131-54
pubmed: 16472210
Angew Chem Int Ed Engl. 2016 Oct 17;55(43):13529-13532
pubmed: 27666731
Chem Pharm Bull (Tokyo). 2020;68(2):117-128
pubmed: 32009078
J Org Chem. 2006 Jan 6;71(1):360-3
pubmed: 16388659
J Nat Prod. 2010 Oct 22;73(10):1727-9
pubmed: 20836516
Org Lett. 2011 Apr 1;13(7):1840-3
pubmed: 21375291

Auteurs

Christopher E Reimann (CE)

Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, 1200 E. California Blvd, MC 101-20, Pasadena, CA, 91125, USA.

Aurapat Ngamnithiporn (A)

Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, 1200 E. California Blvd, MC 101-20, Pasadena, CA, 91125, USA.
Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Bangkok, 10210, Thailand.

Kohei Hayashida (K)

Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, 1200 E. California Blvd, MC 101-20, Pasadena, CA, 91125, USA.
Discovery Research Laboratories, Nippon Chemiphar Co., Ltd., 1-22 Hikokawado, Misato, Saitama, 341-005, Japan.

Daisuke Saito (D)

Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, 1200 E. California Blvd, MC 101-20, Pasadena, CA, 91125, USA.
Discovery Research Laboratories, Nippon Chemiphar Co., Ltd., 1-22 Hikokawado, Misato, Saitama, 341-005, Japan.

Katerina M Korch (KM)

Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, 1200 E. California Blvd, MC 101-20, Pasadena, CA, 91125, USA.

Brian M Stoltz (BM)

Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, 1200 E. California Blvd, MC 101-20, Pasadena, CA, 91125, USA.
ORCID: 0000-0001-9837-1528

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Classifications MeSH

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