Literature DB >> 26353936

Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.

Barry M Trost1, Maksim Osipov2.   

Abstract

The communesin alkaloids are a diverse family of Penicillium-derived alkaloids. Their caged-polycyclic structure and intriguing biological profiles have made these natural products attractive targets for total synthesis. Similarly, the ascidian-derived alkaloid, perophoramidine, is structurally related to the communesins and has also become a popular target for total synthesis. This review serves to summarize the many elegant approaches that have been developed to access the communesin alkaloids and perophoramidine. Likewise, strategies to access the communesin ring system are reviewed.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkaloids; communesin; perophoramidine; total synthesis; vicinal quaternary stereocenters

Mesh：

Substances：

Year:  2015        PMID： 26353936      PMCID： PMC4698125          DOI： 10.1002/chem.201501735

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  46 in total

1.  An approach to the total synthesis of the marine ascidian metabolite perophoramidine via a halogen-selective tandem Heck/carbonylation strategy.

Authors:  Gerald D Artman; Steven M Weinreb
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

2.  Total synthesis of the polycyclic fungal metabolite (+/-)-communesin F.

Authors:  Peng Liu; Jae Hong Seo; Steven M Weinreb
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-08       Impact factor: 15.336

3.  The Alkaloids of Psychotria rostrata.

Authors:  N H Lajis; Z Mahmud; R F Toia
Journal:  Planta Med       Date:  1993-08       Impact factor: 3.352

Review 4.  It all began with an error: the nomofungin/communesin story.

Authors:  Peter Siengalewicz; Tanja Gaich; Johann Mulzer
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Total synthesis of (±)-aspidophylline A.

Authors:  Liansuo Zu; Ben W Boal; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-05-18       Impact factor: 15.419

6.  Synthetic studies on perophoramidine and the communesins: construction of the vicinal quaternary stereocenters.

Authors:  Jae Hong Seo; Gerald D Artman; Steven M Weinreb
Journal:  J Org Chem       Date:  2006-11-10       Impact factor: 4.354

7.  Interrupted Fischer indolization approach toward the communesin alkaloids and perophoramidine.

Authors:  Alex W Schammel; Grace Chiou; Neil K Garg
Journal:  Org Lett       Date:  2012-08-20       Impact factor: 6.005

8.  Highly enantio- and diastereoselective generation of two quaternary centers in spirocyclopropanation of oxindole derivatives.

Authors:  Artur Noole; Natalia S Sucman; Mikhail A Kabeshov; Tõnis Kanger; Fliur Z Macaev; Andrei V Malkov
Journal:  Chemistry       Date:  2012-10-30       Impact factor: 5.236

9.  A diastereodivergent synthetic strategy for the syntheses of communesin F and perophoramidine.

Authors:  Seo-Jung Han; Florian Vogt; Shyam Krishnan; Jeremy A May; Michele Gatti; Scott C Virgil; Brian M Stoltz
Journal:  Org Lett       Date:  2014-06-09       Impact factor: 6.005

10.  A Catalytic Asymmetric Total Synthesis of (-)-Perophoramidine.

Authors:  B M Trost; M Osipov; S Krüger; Y Zhang
Journal:  Chem Sci       Date:  2015-01-01       Impact factor: 9.825
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  9 in total

1.  Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F.

Authors:  Stephen P Lathrop; Matthew Pompeo; Wen-Tau T Chang; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-06-14       Impact factor: 15.419

2.  Synthesis of 3,3'-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates.

Authors:  Arijit A Adhikari; Léa Radal; John D Chisholm
Journal:  Synlett       Date:  2017-07-11       Impact factor: 2.454

3.  Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.

Authors:  Robert B Susick; Lucas A Morrill; Elias Picazo; Neil K Garg
Journal:  Synlett       Date:  2017       Impact factor: 2.454

4.  Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.

Authors:  Kuan-Lin Chen; Chen-Yu Lai; Mai-Truc Pham; Rong-Jie Chein; Yi Tang; Hsiao-Ching Lin
Journal:  Org Lett       Date:  2020-04-03       Impact factor: 6.005

5.  Expedient Synthesis of Indolo[2,3-b]quinolines, Chromeno[2,3-b]indoles, and 3-Alkenyl-oxindoles from 3,3'-Diindolylmethanes and Evaluation of Their Antibiotic Activity against Methicillin-Resistant Staphylococcus aureus.

Authors:  Chandrasekhar Challa; Jaice Ravindran; Mohini Mohan Konai; Sunil Varughese; Jubi Jacob; B S Dileep Kumar; Jayanta Haldar; Ravi S Lankalapalli
Journal:  ACS Omega       Date:  2017-08-30

6.  Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives.

Authors:  Matthew M Pompeo; Jaime H Cheah; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2019-08-30       Impact factor: 15.419

7.  1-Alkyl-3-alkylindolin-2-imine hydrochlorides as useful building blocks in the copper-catalyzed synthesis of polycyclic indoline scaffolds.

Authors:  Can Liu; Haijun Yang; Changjin Zhu; Hua Fu
Journal:  RSC Adv       Date:  2019-03-14       Impact factor: 3.361

8.  Taming Radical Pairs in the Crystalline Solid State: Discovery and Total Synthesis of Psychotriadine.

Authors:  Jordan J Dotson; Ieva Liepuoniute; J Logan Bachman; Vince M Hipwell; Saeed I Khan; K N Houk; Neil K Garg; Miguel A Garcia-Garibay
Journal:  J Am Chem Soc       Date:  2021-03-08       Impact factor: 15.419

9.  Synthesis of tetracyclic spiroindolines by an interrupted Bischler-Napieralski reaction: total synthesis of akuammicine.

Authors:  Matteo Faltracco; Eelco Ruijter
Journal:  Org Biomol Chem       Date:  2021-11-18       Impact factor: 3.876
  9 in total

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