Literature DB >> 23789841

Photoassisted synthesis of enantiopure alkaloid mimics possessing unprecedented polyheterocyclic cores.

N N Bhuvan Kumar1, Olga A Mukhina, Andrei G Kutateladze.   

Abstract

Enantiopure alkaloid mimics are synthesized via high yielding intramolecular cycloadditions of photogenerated azaxylylenes tethered to pyrroles, with further growth of molecular complexity via post-photochemical transformations of primary photoproducts. This expeditious access to structurally unprecedented polyheterocyclic cores is being developed in the context of diversity-oriented synthesis, as the modular design allows for rapid "pre-assembly" of diverse photoprecursors from simple building blocks/diversity inputs.

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Year:  2013        PMID： 23789841      PMCID： PMC3763736          DOI： 10.1021/ja4042109

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  14 in total

1.  Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors:  Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

2.  Total synthesis of kapakahine E and F.

Authors:  Vinson R Espejo; Jon D Rainier
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

3.  Chaetominine, a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015.

Authors:  Rui H Jiao; Shu Xu; Jun Y Liu; Hui M Ge; Hui Ding; Chen Xu; Hai L Zhu; Ren X Tan
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

4.  Enantiospecific total syntheses of kapakahines B and F.

Authors:  Timothy Newhouse; Chad A Lewis; Phil S Baran
Journal:  J Am Chem Soc       Date:  2009-05-13       Impact factor: 15.419

5.  Rapid photoassisted access to N,O,S-polyheterocycles with benzoazocine and hydroquinoline cores: intramolecular cycloadditions of photogenerated azaxylylenes.

Authors:  Olga A Mukhina; N N Bhuvan Kumar; Teresa M Arisco; Roman A Valiulin; Greg A Metzel; Andrei G Kutateladze
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-31       Impact factor: 15.336

6.  Structure, bioactivity and synthesis of natural products with hexahydropyrrolo[2,3-b]indole.

Authors:  Pau Ruiz-Sanchis; Svetlana A Savina; Fernando Albericio; Mercedes Álvarez
Journal:  Chemistry       Date:  2011-01-12       Impact factor: 5.236

7.  Total synthesis of chaetominine.

Authors:  Mathieu Toumi; François Couty; Jérome Marrot; Gwilherm Evano
Journal:  Org Lett       Date:  2008-10-11       Impact factor: 6.005

8.  Escape from flatland: increasing saturation as an approach to improving clinical success.

Authors:  Frank Lovering; Jack Bikker; Christine Humblet
Journal:  J Med Chem       Date:  2009-11-12       Impact factor: 7.446

9.  Synthesis of (-)-chaetominine.

Authors:  Barry B Snider; Xiaoxing Wu
Journal:  Org Lett       Date:  2007-10-18       Impact factor: 6.005

10.  A straightforward total synthesis of (-)-chaetominine.

Authors:  Beatrice Malgesini; Barbara Forte; Daniela Borghi; Francesca Quartieri; Cesare Gennari; Gianluca Papeo
Journal:  Chemistry       Date:  2009-08-10       Impact factor: 5.236
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  9 in total

1.  Oxazolines as Dual-Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones.

Authors:  Olga A Mukhina; Andrei G Kutateladze
Journal:  J Am Chem Soc       Date:  2016-02-16       Impact factor: 15.419

2.  Regiodivergent Photocyclization of Dearomatized Acylphloroglucinols: Asymmetric Syntheses of (-)-Nemorosone and (-)-6-epi-Garcimultiflorone A.

Authors:  Saishuai Wen; Jonathan H Boyce; Sunil K Kandappa; Jayaraman Sivaguru; John A Porco
Journal:  J Am Chem Soc       Date:  2019-07-02       Impact factor: 15.419

3.  Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles.

Authors:  Olga A Mukhina; Dmitry M Kuznetsov; Teresa M Cowger; Andrei G Kutateladze
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-30       Impact factor: 15.336

4.  Conformationally Constrained Penta(hetero)cyclic Molecular Architectures via Photoassisted Diversity-Oriented Synthesis.

Authors:  Weston J Umstead; Olga A Mukhina; Dr Andrei G Kutateladze
Journal:  European J Org Chem       Date:  2015-04-01

5.  Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza-o-xylylenes via an Unprecedented [2+4] Reaction Topology.

Authors:  Dmitry M Kuznetsov; Olga A Mukhina; Andrei G Kutateladze
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-21       Impact factor: 15.336

6.  Photoassisted access to complex polyheterocycles containing a β-lactam moiety.

Authors:  Weston J Umstead; Olga A Mukhina; Andrei G Kutateladze
Journal:  J Photochem Photobiol A Chem       Date:  2016-07-07       Impact factor: 4.291

7.  Photoinduced Cycloadditions in the Diversity-Oriented Synthesis Toolbox: Increasing Complexity with Straightforward Postphotochemical Modifications.

Authors:  Weston J Umstead; Olga A Mukhina; N N Bhuvan Kumar; Andrei G Kutateladze
Journal:  Aust J Chem       Date:  2015-07-24       Impact factor: 1.321

8.  Photoassisted diversity-oriented synthesis: accessing 2,6-epoxyazocane (oxamorphan) cores.

Authors:  Olga A Mukhina; N N Bhuvan Kumar; Teresa M Cowger; Andrei G Kutateladze
Journal:  J Org Chem       Date:  2014-11-05       Impact factor: 4.354

9.  Ti(Oi-Pr)4-promoted photoenolization Diels-Alder reaction to construct polycyclic rings and its synthetic applications.

Authors:  Baochao Yang; Kuaikuai Lin; Yingbo Shi; Shuanhu Gao
Journal:  Nat Commun       Date:  2017-09-20       Impact factor: 14.919
  9 in total

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