Literature DB >> 30994212

Total Synthesis of Aspidosperma and Strychnos Alkaloids through Indole Dearomatization.

Jordy M Saya1, Eelco Ruijter1, Romano V A Orru1.   

Abstract

Monoterpenoid indole alkaloids are the major class of tryptamine-derived alkaloids found in nature. Together with their structural complexity, this has attracted great interest from synthetic organic chemists. In this Review, the syntheses of Aspidosperma and Strychnos alkaloids through dearomatization of indoles are discussed.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkaloids; biomimetic synthesis; dearomatization; indoles; natural product synthesis

Mesh：

Substances：

Year:  2019        PMID： 30994212     DOI： 10.1002/chem.201901130

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


  11 in total

1.  Directed Palladium-Catalyzed Acetoxylation of Indolines. Total Synthesis of N-Benzoylcylindrocarine.

Authors:  Kristen M Flynn; Kolby L White; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2022-01-25       Impact factor: 4.198

2.  Total Synthesis of (-)-Voacinol and (-)-Voacandimine C.

Authors:  Kristen M Flynn; In-Soo Myeong; Taylor Pinto; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2022-05-11       Impact factor: 16.383

3.  Diversification of Nucleophile-Intercepted Beckmann Fragmentation Products and Related Density Functional Theory Studies.

Authors:  Leah L Lowder; Fengyue Zhao; Mathes M Vaughan; K N Houk; Fang Liu; Jimmy Wu
Journal:  J Org Chem       Date:  2020-08-26       Impact factor: 4.354

4.  Total Synthesis of (-)-Strictosidine and Interception of Aryne Natural Product Derivatives "Strictosidyne" and "Strictosamidyne".

Authors:  Sarah M Anthony; Veronica Tona; Yike Zou; Lucas A Morrill; John M Billingsley; Megan Lim; Yi Tang; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2021-05-06       Impact factor: 15.419

5.  Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- and C3-Borylated Indolines.

Authors:  Grace L Trammel; Rositha Kuniyil; Phillip F Crook; Peng Liu; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2021-09-28       Impact factor: 16.383

6.  Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction.

Authors:  Matteo Faltracco; Said Ortega-Rosales; Elwin Janssen; Răzvan C Cioc; Christophe M L Vande Velde; Eelco Ruijter
Journal:  Org Lett       Date:  2021-03-31       Impact factor: 6.005

7.  Hypoiodite-Catalyzed Oxidative Umpolung of Indoles for Enantioselective Dearomatization.

Authors:  Hiroki Tanaka; Naoya Ukegawa; Muhammet Uyanik; Kazuaki Ishihara
Journal:  J Am Chem Soc       Date:  2022-03-23       Impact factor: 15.419

8.  Access to N-unprotected 2-amide-substituted indoles from Ugi adducts via palladium-catalyzed intramolecular cyclization of o-iodoanilines bearing furan rings.

Authors:  Hui Peng; Kai Jiang; Guangjin Zhen; Furong Wang; Biaolin Yin
Journal:  RSC Adv       Date:  2020-03-23       Impact factor: 3.361

9.  Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade.

Authors:  James A Rossi-Ashton; Aimee K Clarke; Richard J K Taylor; William P Unsworth
Journal:  Org Lett       Date:  2020-01-15       Impact factor: 6.005

10.  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
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