Literature DB >> 25684829

Syntheses of Cyclic Guanidine-Containing Natural Products.

Yuyong Ma1, Saptarshi De1, Chuo Chen1.   

Abstract

Naturally occurring guanidine derivatives frequently display medicinally useful properties. Among them, the higher order pyrrole-imidazole alkaloids, the dragmacidins, the crambescidins/batzelladines, and the saxitoxins/tetradotoxins have stimulated the development of many new synthetic methods over the past decades. We provide here an overview of the syntheses of these cyclic guanidine-containing natural products.

Entities:  

Keywords:  Alkaloids; Guanidine; Natural Products; Total Synthesis

Year:  2015        PMID： 25684829      PMCID： PMC4325426          DOI： 10.1016/j.tet.2014.11.056

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  253 in total

1.  Enantiospecific formal total synthesis of the tumor and GSK-3 beta inhibiting alkaloid, (-)-agelastatin A.

Authors:  Karl J Hale; Mathias M Domostoj; Derek A Tocher; Ed Irving; Feodor Scheinmann
Journal:  Org Lett       Date:  2003-08-07       Impact factor: 6.005

2.  Extending Pummerer reaction chemistry: application to the assembly of the pentacyclic core of dibromopalau'amine.

Authors:  Ken S Feldman; Ahmed Yimam Nuriye
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

3.  A short total synthesis of the marine sponge pyrrole-2-aminoimidazole alkaloid (±)-agelastatin A.

Authors:  Petar A Duspara; Robert A Batey
Journal:  Angew Chem Int Ed Engl       Date:  2013-08-22       Impact factor: 15.336

4.  Dragmacidins: new protein phosphatase inhibitors from a southern australian deep-water marine sponge, spongosorites sp

Authors: 
Journal:  J Nat Prod       Date:  1998-05       Impact factor: 4.050

Review 5.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

6.  Synthetic approach towards tetrodotoxin. I. Diels-Alder reaction of alpha-oximinoethylbenzooquinones with butadiene.

Authors:  Y Kishi; F Nakatsubo; M Aratani; T Goto; S Inoue
Journal:  Tetrahedron Lett       Date:  1970-12       Impact factor: 2.415

Review 7.  Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors:  Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal:  Nat Prod Rep       Date:  2011-05-09       Impact factor: 13.423

8.  Revisiting the Kinnel-Scheuer hypothesis for the biosynthesis of palau'amine.

Authors:  Zhiqiang Ma; Jianming Lu; Xiao Wang; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2010-09-16       Impact factor: 6.222

9.  Enantioselective total synthesis of (+)-dibromophakellstatin.

Authors:  Karine G Poullennec; Daniel Romo
Journal:  J Am Chem Soc       Date:  2003-05-28       Impact factor: 15.419

10.  Density functional theory guided design of exo-selective dehydroalanine dienophiles for application toward the synthesis of palau'amine.

Authors:  Timothy A Cernak; James L Gleason
Journal:  J Org Chem       Date:  2007-12-08       Impact factor: 4.354
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  18 in total

Review 1.  Structure, synthesis and biological properties of the pentacyclic guanidinium alkaloids.

Authors:  Yunlong Shi; Yasamin Moazami; Joshua G Pierce
Journal:  Bioorg Med Chem       Date:  2017-03-12       Impact factor: 3.641

2.  Rapid access to the core skeleton of the [3 + 2]-type dimeric pyrrole-imidazole alkaloids by triplet ketone-mediated C-H functionalization.

Authors:  Lin You; Chuo Chen
Journal:  Tetrahedron       Date:  2017-12-15       Impact factor: 2.457

3.  Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes.

Authors:  Artur K Mailyan; Kyle Young; Joanna L Chen; Bradley T Reid; Armen Zakarian
Journal:  Org Lett       Date:  2016-10-25       Impact factor: 6.005

4.  Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation.

Authors:  Bradley T Reid; Artur K Mailyan; Armen Zakarian
Journal:  J Org Chem       Date:  2018-06-22       Impact factor: 4.354

5.  Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net (3 + 2) and (4 + 3) Cycloadditions.

Authors:  V Raghavendra Rao Kovvuri; Haoran Xue; Daniel Romo
Journal:  Org Lett       Date:  2020-02-03       Impact factor: 6.005

6.  Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions.

Authors:  Luke J Peterson; Jingyi Luo; John P Wolfe
Journal:  Org Lett       Date:  2017-05-23       Impact factor: 6.005

7.  Natural products as inspiration for the development of new synthetic methods.

Authors:  Zhiqiang Ma; Chuo Chen
Journal:  J Chin Chem Soc       Date:  2017-08-09       Impact factor: 1.967

8.  Thio acid-mediated conversion of azides to amides - exploratory studies en route to oroidin alkaloids.

Authors:  Apsara K Herath; Manoj R Bhandari; Delphine Gout; Muhammed Yousufuddin; Carl J Lovely
Journal:  Tetrahedron Lett       Date:  2017-08-24       Impact factor: 2.415

9.  Preparation and Diels-Alder reactions of 1'-heterosubsituted vinylimidazoles.

Authors:  Abhisek Ray; Sabuj Mukherjee; Jayanta Das; Manoj K Bhandari; Hongwang Du; Muhammed Yousufuddin; Carl J Lovely
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

10.  Syntheses of Sceptrins and Nakamuric Acid and Insights into the Biosyntheses of Pyrrole-Imidazole Dimers.

Authors:  Xiaolei Wang; Yang Gao; Zhiqiang Ma; Rodrigo A Rodriguez; Zhi-Xiang Yu; Chuo Chen
Journal:  Org Chem Front       Date:  2015-08-01       Impact factor: 5.281
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