Rapid entry to phenanthroindolizidine alkaloids <i>via</i> an acid-catalysed acyliminium ion-electrocyclization cascade-Reference-Cited by-同舟云学术

Rapid entry to phenanthroindolizidine alkaloids via an acid-catalysed acyliminium ion-electrocyclization cascade

Published:2023 Issue:40 Volume:21 Page:8075-8078
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

St. Pierre Max¹^ORCID,Kempthorne Christine J.²,Liscombe David K.²,McNulty James¹^ORCID

Affiliation:

1. Department of Chemistry & Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario L8S 4M1, Canada

2. Vineland Research and Innovation Centre, 4890 Victoria Ave North, Box 4000, Vineland Station, Ontario L0R 2E0, Canada

Abstract

A synthesis of phenanthroindolizidine alkaloids was achieved via an acid catalysed deprotection-condensation-electrocyclization cascade. This provided a concise synthesis of (±)-seco-antofine and (±)-septicine in 4 steps and with high overall yields.

Funder

Natural Sciences and Engineering Research Council of Canada

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/OB/D3OB01359F

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1. Ethnobotany, Phytochemistry and Pharmacological Effects of Plants in Genus Cynanchum Linn. (Asclepiadaceae)

2. Possible pharmaceutical applications can be developed from naturally occurring phenanthroindolizidine and phenanthroquinolizidine alkaloids

3. Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkaloids for Anti-Cancer Therapy

4. In Vitro Cytotoxic Activity of Phenanthroindolizidine Alkaloids from Cynanchum vincetoxicum and Tylophora tanakae against Drug-Sensitive and Multidrug-Resistant Cancer Cells

5. Anti-proliferative activity and suppression of P-glycoprotein by (−)-antofine, a natural phenanthroindolizidine alkaloid, in paclitaxel-resistant human lung cancer cells

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