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Literature DB >> 23477843

Application of in situ-generated Rh-bound trimethylenemethane variants to the synthesis of 3,4-fused pyrroles.

Abstract

Rh-bound trimethylenemethane variants generated from the interaction of a Rh-carbenoid with an allene have been applied to the synthesis of substituted 3,4-fused pyrroles. The pyrrole products are useful starting points for the syntheses of various dipyrromethene ligands. Furthermore, the methodology has been applied to a synthesis of the natural product cycloprodigiosin, which demonstrates antitumor and immunosuppressor activity.

Entities: Chemical

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Year: 2013 PMID： 23477843 DOI： 10.1021/ja401380d

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

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Cited

18 in total

1. Elimination of butylcycloheptylprodigiosin as a known natural product inspired by an evolutionary hypothesis for cyclic prodigiosin biosynthesis.

Authors: Brian T Jones; Dennis X Hu; Brett M Savoie; Regan J Thomson
Journal: J Nat Prod Date: 2013-09-20 Impact factor: 4.050

2. Catalytic asymmetric transannulation of NH-1,2,3-triazoles with olefins.

Authors: Sen Wai Kwok; Li Zhang; Neil P Grimster; Valery V Fokin
Journal: Angew Chem Int Ed Engl Date: 2014-03-24 Impact factor: 15.336

3. Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: a general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines.

Authors: Yi Shi; Anton V Gulevich; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2014-10-21 Impact factor: 15.336

4. Expedient synthesis of fused azepine derivatives using a sequential rhodium(II)-catalyzed cyclopropanation/1-aza-Cope rearrangement of dienyltriazoles.

Authors: Erica E Schultz; Vincent N G Lindsay; Richmond Sarpong
Journal: Angew Chem Int Ed Engl Date: 2014-07-15 Impact factor: 15.336

5. Enantioselective synthesis of metacycloprodigiosin via the "Wasserman pyrrole".

Authors: Marvin M Vega; Diana M Crain; Leah C Konkol; Regan J Thomson
Journal: Tetrahedron Lett Date: 2015-06-03 Impact factor: 2.415

6. Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.

Authors: Liangbing Fu; Huw M L Davies
Journal: Org Lett Date: 2017-03-30 Impact factor: 6.005

Application of in situ-generated Rh-bound trimethylenemethane variants to the synthesis of 3,4-fused pyrroles.

1. Elimination of butylcycloheptylprodigiosin as a known natural product inspired by an evolutionary hypothesis for cyclic prodigiosin biosynthesis.

2. Catalytic asymmetric transannulation of NH-1,2,3-triazoles with olefins.

3. Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: a general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines.

4. Expedient synthesis of fused azepine derivatives using a sequential rhodium(II)-catalyzed cyclopropanation/1-aza-Cope rearrangement of dienyltriazoles.

5. Enantioselective synthesis of metacycloprodigiosin via the "Wasserman pyrrole".

6. Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.

7. Intramolecular transannulation of alkynyl triazoles via alkyne-carbene metathesis step: access to fused pyrroles.

8. Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes.

Review 9. Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products.

10. Regiodivergent synthesis of pyrazino-indolines vs. triazocines via α-imino carbenes addition to imidazolidines.