Total synthesis of protosappanin A and its derivatives via palladium catalyzed ortho C–H activation/C–C cyclization under microwave irradiation

2016 ◽  
Vol 52 (29) ◽  
pp. 5152-5155 ◽  
Author(s):  
Jiaqi Liu ◽  
Xuan Zhou ◽  
Chenglong Wang ◽  
Wanyong Fu ◽  
Wenyi Chu ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Total Synthesis ◽  
Natural Product ◽  
Ring Enlargement ◽  
Palladium Catalyzed

Protosappanin A, a complex natural product with high bioactivity, and 25 of its derivatives were synthesized through an intramolecular ortho C–H activation/C–C cyclization, ring-enlargement and deprotection reaction. C–H activation as the key step was investigated and optimized.

Application of palladium-catalyzed aryl C–H alkylation in total synthesis of (−)-berkelic acid

2021 ◽  
Vol 8 (1) ◽  
pp. 82-86
Author(s):  
Hui-Hong Wang ◽  
Xiao-Dong Wang ◽  
Fei Cao ◽  
Wei-Wei Gao ◽  
Shu-Meng Ma ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Berkelic Acid ◽  
Palladium Catalyzed

Total synthesis of the isochroman natural product (–)-berkelic acid.

Enantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B

2014 ◽  
Vol 12 (31) ◽  
pp. 5883-5890 ◽  
Author(s):  
Jeffrey Buter ◽  
Renée Moezelaar ◽  
Adriaan J. Minnaard
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Conjugate Addition ◽  
Natural Product Synthesis ◽  
Conjugate Additions ◽  
Arylboronic Acids ◽  
Cyclic Enones ◽  
Palladium Catalyzed

Palladium catalyzed asymmetric conjugate addition of ortho-substituted arylboronic acids to cyclic enones and its application in natural product synthesis.

Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A

2001 ◽  
Vol 79 (11) ◽  
pp. 1562-1592 ◽  
Author(s):  
Oren P Anderson ◽  
Anthony GM Barrett ◽  
Jeremy J Edmunds ◽  
Shun-Ichiro Hachiya ◽  
James A Hendrix ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Marine Natural Product ◽  
Aldol Reactions ◽  
Calyculin A ◽  
Coupling Reactions ◽  
Stille Coupling ◽  
Palladium Catalyzed ◽  
Key Steps ◽  
Absolute Stereochemistry

The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth–Meyers approach to the synthesis of the oxazole fragment.Key words: calyculin, marine natural product, phosphatase inhibitor, total synthesis, palladium catalyzed coupling reactions, allylboration reactions, aldol reactions, spiroketal, Cornforth–Meyers oxazole reaction.

Progress Toward The Total Synthesis Of The Marine Natural Product Karlotoxin 5

Planta Medica ◽  
2013 ◽  
Vol 79 (10) ◽  
Author(s):  
M Albadry ◽  
Y Zou ◽  
Y Takahashi ◽  
A Waters ◽  
M Hossein ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Marine Natural Product

Total Synthesis of the Antitumor Depsipeptide FE399 and its S-Benzyl Derivative: A Macrolactamization Approach

2020 ◽  
Author(s):  
Takayuki Tonoi ◽  
Miyuki Ikeda ◽  
Teruyuki Sato ◽  
Ryo Kawahara ◽  
Takatsugu Murata ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Total Synthesis ◽  
Natural Product ◽  
Condensation Reaction ◽  
Practical Method ◽  
Equilibrium Mixture ◽  
Conformational Isomers ◽  
Single Isomer

<div>An efficient and practical method for the synthesis of (9R,14R,17R)-FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2-methyl-6-nitrobenzoic anhydride (MNBA)-mediated dehydration condensation reaction was effectively employed for the formation of the 16-membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S-benzyl product and isolated as a single isomer. Thus, we could confirm that the molecular structure of FE399 obtained by this method is identical to that of the natural product.</div>

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid

2019 ◽  
Author(s):  
Timothy Newhouse ◽  
Aneta Turlik ◽  
Yifeng Chen ◽  
Anthony Scruse
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Membered Ring ◽  
Entry Point ◽  
Ketone Reduction ◽  
Coupling Approach

<div> <p>The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product is constructed via a convergent fragment coupling approach, wherein the central 7-membered ring is synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction. Strategic reductions include a diastereoselective SmI<sub>2</sub>-mediated ketone reduction with PhSH and a new protocol for selective ester reduction in the presence of ketones. The convergent strategy reported herein may be an entry point to the larger class of kaurane diterpenoids.</p> </div>

A Short Synthesis of (+)-Brefeldin C via Enantioselective Radical Hydroalkynylation

2019 ◽  
Author(s):  
Lars Gnägi ◽  
Severin Vital Martz ◽  
Daniel Meyer ◽  
Robin Marc Schärer ◽  
Philippe Renaud
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Oxidation State ◽  
Single Step ◽  
Radical Process ◽  
Target Molecule ◽  
Short Synthesis ◽  
The One

<div><div><div><div><p>A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows to achieve a high trans diastereoselectivity during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis require six product purifications and it provides (+)-brefeldin C in 18% overall yield.</p></div></div></div></div>

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