A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine

Synthesis ◽  
2018 ◽  
Vol 51 (07) ◽  
pp. 1611-1622 ◽  
Author(s):  
Alexey Fedorov ◽  
Ekaterina Shchegravina ◽  
Elena Svirshchevskaya ◽  
Hans-Günther Schmalz
Keyword(s):  
Synthetic Approach ◽  
Ring Contraction ◽  
Sandmeyer Reaction ◽  
Fischer Indole Synthesis ◽  
Naturally Occurring ◽  
Curtius Reaction ◽  
Indole Synthesis

A six-step semisynthetic approach towards chiral nonracemic pyrrolo-allocolchicinoids starting from naturally occurring colchicine was developed. The synthetic scheme includes an electrocyclic tropolone ring contraction to afford allocolchicinic acid followed by the Curtius reaction, giving the corresponding aniline. The Sandmeyer reaction and copper-mediated hydrazination gave hydrazine-substituted allocolchicine. This was introduced into the Fischer indole synthesis, affording libraries of regioisomeric indole-based allocolchicine congeners.

Modular Counter-Fischer–Indole Synthesis through Radical-Enolate Coupling

2021 ◽  
Vol 23 (3) ◽  
pp. 1096-1102
Author(s):  
Hyunho Chung ◽  
Jeongyun Kim ◽  
Gisela A. González-Montiel ◽  
Paul Ha-Yeon Cheong ◽  
Hong Geun Lee
Keyword(s):  
Fischer Indole Synthesis ◽  
Indole Synthesis

A continuous flow microwave-assisted fischer indole synthesis of 7-Ethyltryptophol

2017 ◽  
Vol 121 ◽  
pp. 144-148 ◽  
Author(s):  
Jianguo Xu ◽  
Jiangang Yu ◽  
Yi Jin ◽  
Jie Li ◽  
Zhiqun Yu ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Microwave Assisted ◽  
Fischer Indole Synthesis ◽  
Indole Synthesis

scholarly journals Total Syntheses of Pladienolide-Derived Spliceosome Modulators

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5938
Author(s):  
Jaehoon Sim ◽  
Eunbin Jang ◽  
Hyun Jin Kim ◽  
Hongjun Jeon
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Features ◽  
Synthetic Approach ◽  
Synthetic Analog ◽  
Phase I Clinical Trials ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Anti Cancer ◽  
Synthetic Approaches

Pladienolides, an emerging class of naturally occurring spliceosome modulators, exhibit interesting structural features, such as highly substituted 12-membered macrocycles and epoxide-containing diene side chains. The potential of pladienolides as anti-cancer agents is confirmed by H3B-8800, a synthetic analog of this natural product class, which is currently under Phase I clinical trials. Since its isolation in 2004 and the first total synthesis in 2007, a dozen total syntheses and synthetic approaches toward the pladienolide class have been reported to date. This review focuses on the eight completed total syntheses of naturally occurring pladienolides or their synthetic analogs, in addition to a synthetic approach to the main framework of the natural product.

scholarly journals Polyphosphate Ester as a Synthetic Agent. V. The Fischer Indole Synthesis with Polyphosphate Ester

1966 ◽  
Vol 14 (9) ◽  
pp. 934-939 ◽  
Author(s):  
Yuichi Kanaoka ◽  
Yoshio Ban ◽  
Koichi Miyashita ◽  
Kimiko Irie ◽  
Osamu Yonemitsu
Keyword(s):  
Fischer Indole Synthesis ◽  
Indole Synthesis

One-Pot Reactions Involving the Fischer Indole Synthesis and Friedel–Crafts Reactions

2018 ◽  
Vol 61 (7-8) ◽  
pp. 685-688 ◽  
Author(s):  
Hien Vuong ◽  
Samantha Duarte ◽  
Douglas A. Klumpp
Keyword(s):  
One Pot ◽  
Fischer Indole Synthesis ◽  
Indole Synthesis
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