Nonbiomimetic total synthesis of indole alkaloids using alkyne-based strategies

2021 ◽  
Vol 19 (16) ◽  
pp. 3551-3568
Author(s):  
Hiroaki Ohno ◽  
Shinsuke Inuki
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Indole Alkaloids ◽  
Natural Product Synthesis ◽  
Total Syntheses

Significance of nonbiomimetic natural product synthesis and nonbiomimetic total syntheses of indole alkaloids based on the construction of core structures using alkyne reactions are summarized in this review.

Total Synthesis of Natural Products Using Intramolecular Nozaki–Hiyama–Takai–Kishi Reactions

Synlett ◽  
2020 ◽  
Vol 31 (05) ◽  
pp. 421-433 ◽  
Author(s):  
Ken-ichi Takao ◽  
Akihiro Ogura ◽  
Keisuke Yoshida ◽  
Siro Simizu
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Total Syntheses

In this Account, we describe our studies on the total synthesis of several natural products using intramolecular Nozaki–Hiyama–Takai–Kishi (NHTK) reactions. In each synthesis, an NHTK reaction is used to efficiently construct a medium-sized ring. These examples demonstrate the utility of the intramolecular NHTK reaction in natural product synthesis.1 Introduction2 Total Synthesis of (+)-Pestalotiopsin A3 Total Synthesis of (+)-Cytosporolide A4 Total Synthesis of (+)-Vibsanin A5 Total Syntheses of (+)-Aquatolide and Related Humulanolides6 Conclusion

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

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.

Combined coinage metal catalysis in natural product synthesis: total synthesis of (+)-varitriol and seven analogs

2012 ◽  
Vol 10 (30) ◽  
pp. 5965 ◽  
Author(s):  
Tao Sun ◽  
Carl Deutsch ◽  
Norbert Krause
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Metal Catalysis ◽  
Coinage Metal

Transition metal-promoted biomimetic steps in total syntheses

2014 ◽  
Vol 31 (4) ◽  
pp. 533-549 ◽  
Author(s):  
Xu-Wen Li ◽  
Bastien Nay
Keyword(s):  
Transition Metal ◽  
Transition Metals ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Total Syntheses

Important biomimetic steps in natural product synthesis have been promoted by transition metals, as exemplified by this beautiful ruthenium-catalyzed rearrangement of an endoperoxide into elysiapyrone A. Such reactions are supposed to occur during the biosynthesis, yet under different catalysis conditions.

Ir-Catalyzed reactions in natural product synthesis

2018 ◽  
Vol 5 (1) ◽  
pp. 132-150 ◽  
Author(s):  
Pengquan Chen ◽  
Yuecheng Wu ◽  
Shifa Zhu ◽  
Huanfeng Jiang ◽  
Zhiqiang Ma
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Catalyzed Reactions

This review highlights the recent applications of Ir-catalyzed reactions in the total synthesis of natural products.

The Total Syntheses of Phorboxazoles — New Classics in Natural Product Synthesis.

ChemInform ◽  
2003 ◽  
Vol 34 (35) ◽  
Author(s):  
Lars Ole Haustedt ◽  
Ingo V. Hartung ◽  
H. M. R. Hoffmann
Keyword(s):  
Natural Product ◽  
Natural Product Synthesis ◽  
Total Syntheses
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