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.

Total Syntheses of Cylindrocyclophanes Exemplifying the Power of Transition-Metal Catalysis in Natural-Product Synthesis

Synlett ◽  
2020 ◽  
Author(s):  
Bernhard Breit ◽  
Dino Berthold
Keyword(s):  
Transition Metal ◽  
Natural Product ◽  
Biological Properties ◽  
Transition Metal Catalysis ◽  
Natural Product Synthesis ◽  
Metal Catalysis ◽  
Total Syntheses ◽  
Key Steps ◽  
Synthetic Approaches ◽  
Cylindrocyclophane A

Cylindrocyclophanes are a class of naturally occurring 22-membered macrocycles with a unique architecture and interesting physical, chemical, and biological properties. This comprehensive account summarizes progress in various synthetic approaches to these compounds during the last twenty years, thereby emphasizing the key steps for establishing the [7,7]-paracyclophane scaffold, as well as alternative approaches to the construction of its stereocenters. Many of these syntheses highlight the power of transition-metal catalysis for natural-product synthesis. Furthermore, the unraveling of the biosynthesis to these natural products in Cylindrospermum licheniforme is discussed.1 Introduction2 Biosynthesis3 Smith’s Synthesis of (–)-Cylindrocyclophanes A and F4 Hoye’s Synthesis of (–)-Cylindrocyclophane A5 Iwabuchi’s Syntheses of (–)-Cylindrocyclophane A and (+)-Cylindrocyclophane A6 Nicolaou’s Synthesis of (–)-Cylindrocyclophanes A and F7 Breit’s Synthesis of (–)-Cylindrocyclophane F8 Conclusion

scholarly journals Recent Developments in Polyene Cyclizations and Their Applications in Natural Product Synthesis

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 67-82 ◽  
Author(s):  
Anthony Barrett ◽  
Tsz-Kan Ma ◽  
Thomas Mies
Keyword(s):  
Transition Metal ◽  
Natural Product ◽  
Lewis Acid ◽  
Multiple Bond ◽  
Natural Product Synthesis ◽  
Cyclization Reactions ◽  
Cascade Cyclizations ◽  
Highly Efficient ◽  
Recent Developments ◽  
Radical Cascade

Cascade polyene cyclization reactions are highly efficient and elegant bioinspired transformations that involve simultaneous multiple bond constructions to rapidly generate complex polycyclic molecules. This review summarizes the most prominent work on a variety of cationic and radical cascade cyclizations and their applications in natural product synthesis published between 2014 and 2018.1 Introduction2 Cationic Polyene Cyclizations2.1 Lewis Acid Mediated Polyene Cyclizations2.2 Brønsted Acid Mediated Polyene Cyclizations2.3 Halogen Electrophile Initiated Polyene Cyclizations2.4 Sulfur Electrophile Initiated Polyene Cyclizations2.5 Transition-Metal-Mediated Cationic Polyene Cyclizations3 Radical Polyene Cyclizations3.1 Transition-Metal-Mediated Radical Polyene Cyclizations3.2 Photocatalyst-Mediated Polyene Cyclizations4 Origin of Stereocontrol in Polyene Cyclizations5 Conclusion

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

scholarly journals Recent Advance of Domino Michael Reaction in Natural Product Synthesis

2021 ◽  
Vol 16 (10) ◽  
pp. 1934578X2110498
Author(s):  
Hisahiro Hagiwara
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Michael Reaction ◽  
Natural Product Synthesis ◽  
Total Syntheses ◽  
Michael Reactions ◽  
Recent Advances ◽  
Key Steps ◽  
Related Compounds

Recent advances in the total syntheses of cyclic natural products and related compounds from 2005 to 2021, which employ domino Michael reactions as key steps, have been reviewed, focusing mainly on the domino Michael reactions catalyzed by organocatalysts.

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

2003 ◽  
Vol 42 (24) ◽  
pp. 2711-2716 ◽  
Author(s):  
Lars Ole Haustedt ◽  
Ingo V. Hartung ◽  
H. M. R. Hoffmann
Keyword(s):  
Natural Product ◽  
Natural Product Synthesis ◽  
Total Syntheses

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 Transition-metal and organocatalysis in natural product synthesis

2013 ◽  
Vol 9 ◽  
pp. 1192-1193 ◽  
Author(s):  
David Yu-Kai Chen ◽  
Dawei Ma
Keyword(s):  
Transition Metal ◽  
Natural Product ◽  
Natural Product Synthesis

Transition metal-catalyzed iodine(iii)-mediated nitrene transfer reactions: efficient tools for challenging syntheses

2017 ◽  
Vol 53 (3) ◽  
pp. 493-508 ◽  
Author(s):  
B. Darses ◽  
R. Rodrigues ◽  
L. Neuville ◽  
M. Mazurais ◽  
P. Dauban
Keyword(s):  
Transition Metal ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Synthetic Methods ◽  
Transfer Reactions ◽  
Nitrene Transfer ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The main synthetic applications of catalytic C(sp3)–H amination and alkene aziridination reactions are discussed in the context of natural product synthesis. The examples highlight that these synthetic methods now firmly belong in the organic chemist's toolbox.

Sign in / Sign up

Export Citation Format

Share Document