Literature DB >> 25081029

Total synthesis of the marine pyridoacridine alkaloid demethyldeoxyamphimedine.

Benedikt Melzer1, Alois Plodek, Franz Bracher.   

Abstract

A four-step total synthesis of the marine pyridoacridine alkaloid demethyldeoxyamphimedine (5) is presented. With an overall yield of 6.4%, this pentacyclic compound has been synthesized by utilizing only two commercial building blocks, ethyl nicotinate and 2-iodoaniline. The final cyclization step was achieved via a directed remote ring metalation with Knochel-Hauser base (TMPMgCl·LiCl) followed by intramolecular trapping of an ester group.

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Year:  2014        PMID： 25081029     DOI： 10.1021/jo501312d

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  7 in total

1.  Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids.

Authors:  Benedikt C Melzer; Alois Plodek; Franz Bracher
Journal:  Beilstein J Org Chem       Date:  2019-09-26       Impact factor: 2.883

2.  An improved high yield total synthesis and cytotoxicity study of the marine alkaloid neoamphimedine: an ATP-competitive inhibitor of topoisomerase IIα and potent anticancer agent.

Authors:  Linfeng Li; Adedoyin D Abraham; Qiong Zhou; Hadi Ali; Jeremy V O'Brien; Brayden D Hamill; John J Arcaroli; Wells A Messersmith; Daniel V LaBarbera
Journal:  Mar Drugs       Date:  2014-09-19       Impact factor: 5.118

Review 3.  New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids.

Authors:  Alois Plodek; Franz Bracher
Journal:  Mar Drugs       Date:  2016-01-26       Impact factor: 5.118

Review 4.  Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity.

Authors:  Louis P Sandjo; Victor Kuete; Maique W Biavatti
Journal:  Beilstein J Org Chem       Date:  2015-09-18       Impact factor: 2.883

5.  A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines.

Authors:  Benedikt C Melzer; Franz Bracher
Journal:  Beilstein J Org Chem       Date:  2017-08-08       Impact factor: 2.883

6.  Palladium-Catalyzed Dehydrogenative Coupling: An Efficient Synthetic Strategy for the Construction of the Quinoline Core.

Authors:  Asier Carral-Menoyo; Verónica Ortiz-de-Elguea; Mikel Martinez-Nunes; Nuria Sotomayor; Esther Lete
Journal:  Mar Drugs       Date:  2017-08-30       Impact factor: 5.118

7.  A Predictive Model Towards Site-Selective Metalations of Functionalized Heterocycles, Arenes, Olefins, and Alkanes using TMPZnCl⋅LiCl.

Authors:  Moritz Balkenhohl; Harish Jangra; Ilya S Makarov; Shu-Mei Yang; Hendrik Zipse; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-08       Impact factor: 16.823
  7 in total

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