Methodology for stereochemical control in bioactive natural product synthesis - new methods toward enediyne antitumor antibiotics

1990 ◽  
Vol 62 (10) ◽  
pp. 2007-2012 ◽  
Author(s):  
M. Isobe ◽  
T. Nishikawa ◽  
Angkana Herunsalee ◽  
T. Tsukiyama ◽  
Yumi Hirose ◽  
...  
Keyword(s):  
Natural Product ◽  
Natural Product Synthesis ◽  
Antitumor Antibiotics ◽  
New Methods ◽  
Stereochemical Control ◽  
Bioactive Natural Product

scholarly journals Development of a Second Generation Palladium-Catalyzed Cycloalkenylation and its Application to Bioactive Natural Product Synthesis

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800
Author(s):  
Masahiro Toyota
Keyword(s):  
Natural Product ◽  
Second Generation ◽  
Natural Product Synthesis ◽  
Total Syntheses ◽  
Palladium Catalyzed ◽  
Oxidative Alkylation ◽  
Bioactive Natural Product

A novel palladium-catalyzed intramolecular oxidative alkylation of unactivated olefins is described. This protocol was devised to solve one of the drawbacks of the original palladium-catalyzed cycloalkenylation that we developed. We call this new procedure the ‘second generation palladium-catalyzed cycloalkenylation’. This protocol has been applied to the total syntheses of cis-195A trans-195A boonein scholareins A C D and α-skytanthine.

scholarly journals Redirecting Photosynthetic Reducing Power toward Bioactive Natural Product Synthesis

2013 ◽  
Vol 2 (6) ◽  
pp. 308-315 ◽  
Author(s):  
Agnieszka Zygadlo Nielsen ◽  
Bibi Ziersen ◽  
Kenneth Jensen ◽  
Lærke Münter Lassen ◽  
Carl Erik Olsen ◽  
...  
Keyword(s):  
Natural Product ◽  
Reducing Power ◽  
Natural Product Synthesis ◽  
Bioactive Natural Product

Metal-Free Photoredox-Catalyzed C–H/C–H Coupling of Arenes Enabled by Interrupted Pummerer Activation

2019 ◽  
Author(s):  
Miles Aukland ◽  
Mindaugas Šiaučiulis ◽  
Adam West ◽  
Gregory Perry ◽  
David Procter
Keyword(s):  
Natural Product ◽  
Selective Reduction ◽  
Cross Coupling ◽  
One Pot ◽  
Complex Molecules ◽  
Pummerer Reaction ◽  
Metal Free ◽  
Bond Forming ◽  
Coupling Partner ◽  
Bioactive Natural Product

<p>Aryl–aryl cross-coupling constitutes one of the most widely used procedures for the synthesis of high-value materials, ranging from pharmaceuticals to organic electronics and conducting polymers. The assembly of (hetero)biaryl scaffolds generally requires multiple steps; coupling partners must be functionalized before the key bond-forming event is considered. Thus, the development of selective C–H arylation processes in arenes, that side-step the need for prefunctionalized partners, is crucial for streamlining the construction of these key architectures. Here we report an expedient, one-pot assembly of (hetero)biaryl motifs using photocatalysis and two non-prefunctionalized arene partners. The approach is underpinned by the activation of a C–H bond in an arene coupling partner using the interrupted Pummerer reaction. A unique pairing of the organic photoredox catalyst and the intermediate dibenzothiophenium salts enables highly selective reduction in the presence of sensitive functionalities. The utility of the metal-free, one-pot strategy is exemplified by the synthesis of a bioactive natural product and the modification of complex molecules of societal importance.</p>

Recent applications of asymmetric organocatalytic annulation reactions in natural product synthesis

2021 ◽  
Author(s):  
Nengzhong Wang ◽  
Zugen Wu ◽  
Junjie Wang ◽  
Nisar Ullah ◽  
Yixin Lu
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Natural Products Synthesis

A comprehensive and updated summary of asymmetric organocatalytic annulation reactions is presented; in particular, the applications of these annulation strategies to natural products synthesis are highlighted.

scholarly journals The Synthesis of Conjugated Bis-Aryl Vinyl Substrates and Their Photoelectrocyclization Reactions towards Phenanthrene Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Jon D. Rainier ◽  
Xuchen Zhao
Keyword(s):  
Natural Product ◽  
Natural Product Synthesis ◽  
Mechanistic Studies ◽  
Efficient Strategy

AbstractThe photoelectrocyclization of conjugated vinyl biaryls has proven to be a valuable and efficient strategy for generating phenanthrene derivatives. Contained in this review is an overview of the mechanism for the transformation and a discussion of the reaction scope with a focus on the electrocyclization itself, rearomatization, and the application of the reaction in natural product synthesis.1 Introduction2 The Synthesis of Conjugated Vinyl Biaryls3 Mechanistic Studies4 Substrate Scope5 Applications6 Conclusions

Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis

2021 ◽  
Author(s):  
K. R. Holman ◽  
A. M. Stanko ◽  
S. E. Reisman
Keyword(s):  
Natural Product ◽  
Bond Formation ◽  
Natural Product Synthesis ◽  
Cascade Cyclizations ◽  
Palladium Catalyzed ◽  
Multiple Rings

This tutorial review highlights the use of palladium-catalyzed cascade cyclizations in natural product synthesis, focusing on cascades that construct multiple rings and form both C–C and C–X (X = O, N) bonds in a single synthetic operation.

scholarly journals Applications of the Horner-Wadsworth-Emmons olefination in modern natural product synthesis

Synthesis ◽  
2021 ◽  
Author(s):  
Dávid Roman ◽  
Maria Sauer ◽  
Christine Beemelmanns
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Reaction Conditions ◽  
Comprehensive Review ◽  
Modern Natural ◽  
Key Steps ◽  
Synthetic Approaches

Here, we have summarized more than 30 representative natural product syntheses published in 2015 to 2020 that employ one or more Horner-Wadsworth-Emmons (HWE) reactions. We comprehensively describe the applied phosphonate reagents, HWE reaction conditions and key steps of the total synthetic approaches. Our comprehensive review will support future synthetic approaches and serve as guideline to find the best HWE conditions for the most complicated natural products known

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