scholarly journals The First Total Synthesis of (±)-Methyl Salvianolate A Using a Convergent Strategy

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 999
Author(s):  
Bo Wang ◽  
Liping Wang ◽  
Ying Peng ◽  
Yiying Pang ◽  
Hesheng Xiao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Large Scale ◽  
Protecting Groups ◽  
Key Features

Herein, a convergent, practicable and first total synthesis of the natural product, (±)-methyl salvianolate A, is reported. The key features of the approach are the use of a Horner–Wadsworth–Emmons reaction and the protection of multiple hydroxyls using silyl protecting groups. The employment of the readily removable silyl protecting groups allows the synthesis of (±)-methyl salvianolate A and its derivatives on a reasonably large scale.

Highly-Efficient Preparation of Key Intermediate of Huperzine A

2014 ◽  
Vol 484-485 ◽  
pp. 157-160
Author(s):  
Kai Ming Xie
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Potential Application ◽  
Large Scale ◽  
Huperzine A ◽  
Synthetic Route ◽  
Alzheimers Disease ◽  
Highly Efficient ◽  
Large Scale Preparation ◽  
Scale Preparation

Huperzine A was approved for curing Alzheimers disease in the early 1990s in China. We explored a highly-efficient synthetic route for the key intermediate in the total synthesis of this natural product. Only common reagents and conditions were involved. So our new route has potential application in large-scale preparation of the key intermediate.

Highly-Efficient Preparation of Key Intermediate of Huperzine A

2013 ◽  
Vol 803 ◽  
pp. 181-184
Author(s):  
Kai Ming Xie
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Potential Application ◽  
Large Scale ◽  
Huperzine A ◽  
Synthetic Route ◽  
Alzheimers Disease ◽  
Highly Efficient ◽  
Large Scale Preparation ◽  
Scale Preparation

Huperzine A was approved for curing Alzheimers disease in the early 1990s in China. We explored a highly-efficient synthetic route for the key intermediate in the total synthesis of this natural product. Only common reagents and conditions were involved. So our new route has potential application in large-scale preparation of the key intermediate.

Formal Synthesis of Kanamienamide

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 964-968 ◽  
Author(s):  
Tao Ye ◽  
Yang Li ◽  
Yian Guo ◽  
Zhengshuang Xu
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Asymmetric Reduction ◽  
Formal Synthesis ◽  
Wittig Olefination ◽  
Key Features

A formal total synthesis of the anticancer natural product kanamienamide has been accomplished. This communication describes two approaches to the macrocyclic core of the natural product. The key features of the route include an efficient macrolactamization, a Corey–Bakshi–Shibata asymmetric reduction, and a Stork–Zhao–Wittig olefination.

scholarly journals DDQ-Promoted Mild and Efficient Metal-Free Oxidative α-Cyanation of N-Acyl/Sulfonyl 1,2,3,4-Tetrahydroisoquinolines

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3223 ◽  
Author(s):  
Hong Kim ◽  
Heesun Yu ◽  
Hyoungsu Kim ◽  
Seok-Ho Kim ◽  
Dongjoo Lee
Keyword(s):  
Total Synthesis ◽  
Ambient Temperature ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Protecting Groups ◽  
Metal Free ◽  
Wide Range ◽  
Iminium Ions ◽  
Synthetic Utility ◽  
Ddq Oxidation

A mild and highly efficient metal-free oxidative α-cyanation of N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) has been accomplished at an ambient temperature via DDQ oxidation and subsequent trapping of N-acyl/sulfonyl iminium ions with (n-Bu)3SnCN. Employing readily removable N-acyl/sulfonyl groups as protecting groups rather than N-aryl ones enables a wide range of applications in natural product synthesis. The synthetic utility of the method was illustrated using a short and efficient formal total synthesis of (±)-calycotomine in three steps.

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.

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