Total Synthesis of Stachyodin A via One-Pot Suzuki Coupling for Quick Construction of Carbon Skeleton

2021 ◽  
Author(s):  
Yuichiro Kawamoto ◽  
Toyoharu Kobayashi ◽  
Hisanaka Ito
Keyword(s):  
Total Synthesis ◽  
Suzuki Coupling ◽  
Carbon Skeleton ◽  
One Pot

scholarly journals Application of sequential proline-catalyzed α-chlorination and aldol reactions in the total synthesis of 1-deoxygalactonojirimycin

2018 ◽  
Vol 96 (2) ◽  
pp. 144-147 ◽  
Author(s):  
Michael Meanwell ◽  
Mathew Sutherland ◽  
Robert Britton
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Single Step ◽  
Carbon Skeleton ◽  
Aldol Reactions ◽  
Protecting Group ◽  
One Pot ◽  
Enantioselective Total Synthesis ◽  
Epoxide Opening ◽  
Structural Analogues

A short enantioselective total synthesis of 1-deoxygalactonojirimycin (migalastat) has been achieved that does not rely on chiral pool starting materials or biocatalysis. Instead, this synthesis exploits a one-pot proline-catalyzed α-chlorination and aldol reaction of a commercially available aldehyde to assemble the entire carbon skeleton in a single step. The key role played by a nitrogen protecting group in the final epoxide opening reaction is highlighted as is the amenability to access structural analogues using this route.

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.

First total synthesis of oteromycin utilizing one-pot four-step cascade reaction strategy

2013 ◽  
Vol 54 (6) ◽  
pp. 506-511 ◽  
Author(s):  
Hiromi Uchiro ◽  
Nobuhiro Shionozaki ◽  
Ryo Tanaka ◽  
Hiroyuki Kitano ◽  
Naoki Iwamura ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Cascade Reaction ◽  
One Pot

ChemInform Abstract: A One-Pot Preparation of Aryl- and Heteroarylcycloalkenes: Application to the Total Synthesis of (.+-.)-Laurokamurene B.

ChemInform ◽  
2010 ◽  
Vol 41 (9) ◽  
Author(s):  
Jean Tallineau ◽  
Georges Bashiardes ◽  
Jean-Marie Coustard ◽  
Frederic Lecornue
Keyword(s):  
Total Synthesis ◽  
One Pot

One‐Pot Synthetic Procedure for2,2′‐Disubstituted Biaryls via the Suzuki Coupling Reaction of Aryl Triflates in a Biphasic Solvent System

2006 ◽  
Vol 36 (24) ◽  
pp. 3809-3820 ◽  
Author(s):  
Masanori Miura ◽  
Takanori Koike ◽  
Tsukasa Ishihara ◽  
Fukushi Hirayama ◽  
Shuichi Sakamoto ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Suzuki Coupling ◽  
Solvent System ◽  
One Pot ◽  
Suzuki Coupling Reaction ◽  
Synthetic Procedure

A One-Pot Preparation of Aryl- and Heteroarylcycloalkenes: Application to the Total Synthesis of (±)-Laurokamurene B

Synlett ◽  
2009 ◽  
Vol 2009 (17) ◽  
pp. 2761-2764 ◽  
Author(s):  
Frédéric Lecornué ◽  
Jean Tallineau ◽  
Georges Bashiardes ◽  
Jean-Marie Coustard
Keyword(s):  
Total Synthesis ◽  
One Pot

ChemInform Abstract: One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling.

ChemInform ◽  
2016 ◽  
Vol 47 (32) ◽  
Author(s):  
Hongxiang Wu ◽  
Baiping Xu ◽  
Yue Li ◽  
Fengying Hong ◽  
Dezhao Zhu ◽  
...  
Keyword(s):  
Suzuki Coupling ◽  
Aromatic Acids ◽  
One Pot ◽  
One Pot Synthesis ◽  
Palladium Catalyzed
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