Salutaridine and its derivatives as thebaine-equivalents in the synthesis of aporphines-Reference-Cited by-同舟云学术

Salutaridine and its derivatives as thebaine-equivalents in the synthesis of aporphines

Published:2013-12-01 Issue:12 Volume:11 Page:2022-2030
ISSN:2391-5420
Container-title:Open Chemistry
language:
Short-container-title:

Author:

Udvardy Antal¹,Sipos Attila²

Affiliation:

1. 1Department of Physical Chemistry, University of Debrecen, P.O. Box 7, H-4010, Debrecen, Hungary

2. 2Department of Pharmaceutical Chemistry, Medical and Health Science Center, University of Debrecen, P.O. Box 70, H-4032, Debrecen, Hungary

Abstract

AbstractHere we report the transformation of tetracyclic morphinan salutaridine (1) into 2,3,10,11-tetrasubstituted (R)-aporphines. This method serves as another chemical proof of the previously verified biosynthetic connection with pentacyclic morphinan-6,8-diene-type thebaine. In the presence of nucleophiles, this procedure could lead to pharmacologically interesting new tetrasubstituted aporphinoids. The enantioselective synthesis of 7S-salutaridinol (2) has been also achieved in order to investigate the acid-catalyzed reactions of this natural morphinan.

Publisher

Walter de Gruyter GmbH

Subject

Materials Chemistry,General Chemistry

Link

http://link.springer.com/content/pdf/10.2478/s11532-013-0330-4.pdf

Reference39 articles.

1. http dx org;Finnema;Top Med Chem,2010

2. http dx org;Granchelli;Org Chem,1980

3. http dx org;Becke;Chem Phys,1993

4. http dx org;Zenk;Nat Prod,1985

5. 444. Investigations on the biosynthesis of morphine alkaloids

Cited by 3 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Proposal for the classification of sinomenine alkaloids;Fitoterapia;2024-01

2. Chemical profiling and quantification of potential active constituents responsible for the antiplasmodial activity of Cissampelos pareira;Journal of Ethnopharmacology;2020-11

3. Total Synthesis of 8,14-Dihydromorphinandienone Alkaloids;Organic Letters;2014-03-05