Literature DB >> 15606098

Intramolecular hetero Diels-Alder (Povarov) approach to the synthesis of the alkaloids luotonin A and camptothecin.

Heather Twin1, Robert A Batey.   

Abstract

[reaction: see text] Pyrrolo[3,4-b]quinolines can be formed through the coupling of anilines with N-propargylic substituted heterocyclic aldehydes in the presence of mild Lewis acid catalysts (Ln(OTf)3). The coupling proceeds through sequential imine formation and a formal intramolecular aza-Diels-Alder (Povarov) reaction. This approach was applied in a total synthesis of luotonin A and a formal synthesis of camptothecin.

Entities:  

Year:  2004        PMID： 15606098     DOI： 10.1021/ol0479848

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Design and Synthesis of Fluorescent Acyclic Nucleoside Phosphonates as Potent Inhibitors of Bacterial Adenylate Cyclases.

Authors:  Petra Břehová; Markéta Šmídková; Jan Skácel; Martin Dračínský; Helena Mertlíková-Kaiserová; Monica P Soto Velasquez; Val J Watts; Zlatko Janeba
Journal:  ChemMedChem       Date:  2016-10-24       Impact factor: 3.466

2.  One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines.

Authors:  Kathryn G Guggenheim; Hannah Toru; Mark J Kurth
Journal:  Org Lett       Date:  2012-06-29       Impact factor: 6.005

3.  Highly efficient synthesis and characterization of the GPR30-selective agonist G-1 and related tetrahydroquinoline analogs.

Authors:  Ritwik Burai; Chinnasamy Ramesh; Marvin Shorty; Ramona Curpan; Cristian Bologa; Larry A Sklar; Tudor Oprea; Eric R Prossnitz; Jeffrey B Arterburn
Journal:  Org Biomol Chem       Date:  2010-03-16       Impact factor: 3.876

4.  Oxone promoted dehydrogenative Povarov cyclization of N-aryl glycine derivatives: an approach towards quinoline fused lactones and lactams.

Authors:  Devidas A More; Ganesh H Shinde; Aslam C Shaikh; M Muthukrishnan
Journal:  RSC Adv       Date:  2019-09-25       Impact factor: 4.036

5.  Design and synthesis of C-aryl angular luotonins via a one-pot aza-Nazarov-Friedlander sequence and their Topo-I inhibition studies along with C-aryl vasicinones and luotonins.

Authors:  Sivappa Rasapalli; Vamshikrishna Reddy Sammeta; Zachary F Murphy; James A Golen; Keli Agama; Yves Pommier; Sergey N Savinov
Journal:  Bioorg Med Chem Lett       Date:  2021-03-30       Impact factor: 2.940

Review 6.  Recent advances in the studies on luotonins.

Authors:  Jing Lu Liang; Hyo Chang Cha; Yurngdong Jahng
Journal:  Molecules       Date:  2011-06-14       Impact factor: 4.411

7.  Weinreb amidation as the cornerstone of an improved synthetic route to A-ring-modified derivatives of luotonin A.

Authors:  Norbert Haider; Simon Nuß
Journal:  Molecules       Date:  2012-09-25       Impact factor: 4.411

8.  Sc(OTf)3-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction.

Authors:  Xabier Jiménez-Aberásturi; Francisco Palacios; Jesús M de Los Santos
Journal:  J Org Chem       Date:  2022-08-16       Impact factor: 4.198

9.  A novel multi-component reaction to imidazo[4,5-g]-quinazolines.

Authors:  Li Li; Qianqian Zhang; Bo Liu; Gang Liu
Journal:  Molecules       Date:  2013-05-16       Impact factor: 4.411

10.  Intramolecular Povarov Reactions for the Synthesis of Chromenopyridine Fused 2-Pyridone Polyheterocycles Binding to α-Synuclein and Amyloid-β Fibrils.

Authors:  Dan E Adolfsson; Mohit Tyagi; Pardeep Singh; Adrian Deuschmann; Jörgen Ådén; Anna L Gharibyan; Sanduni Wasana Jayaweera; Anders E G Lindgren; Anders Olofsson; Fredrik Almqvist
Journal:  J Org Chem       Date:  2020-10-25       Impact factor: 4.354
  10 in total

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