scholarly journals Concise total synthesis of two marine natural nucleosides: trachycladines A and B

2014 ◽  
Vol 10 ◽  
pp. 1681-1685 ◽  
Author(s):  
Haixin Ding ◽  
Wei Li ◽  
Zhizhong Ruan ◽  
Ruchun Yang ◽  
Zhijie Mao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Starting Material ◽  
Chemoenzymatic Synthesis ◽  
Critical Step ◽  
Adenylate Deaminase

We report the first total synthesis of trachycladines A (10 steps, 34.2% overall yield) and B (11 steps, 35.0% overall yield) by using 5-deoxy-1,2,3-tri-O-acetyl-β-D-ribofuranose as the starting material. The critical step was the SnCl4assisted regio- and steroselective deprotection of perbenzylated 1-O-methyl-5-deoxyribofuranose. The enzyme adenylate deaminase (EC 3.5.4.6) was successfully applied to the chemoenzymatic synthesis of trachycladines B.

Synthesis of the spirosesquiterpene (−)-acorenone and related cyclopentanoid monoterpenes

1978 ◽  
Vol 56 (12) ◽  
pp. 1628-1633 ◽  
Author(s):  
Gordon L. Lange ◽  
Eli E. Neidert ◽  
Will J. Orrom ◽  
David J. Wallace
Keyword(s):  
Acetic Acid ◽  
Total Synthesis ◽  
Absolute Configuration ◽  
Optically Active ◽  
Starting Material ◽  
Critical Step ◽  
Naturally Occurring ◽  
Toluenesulfonic Acid ◽  
Methylmagnesium Iodide ◽  
Cyclopentanoid Monoterpenes

The first total synthesis of the spirosesquiterpene (−)-acorenone (1) is described. The critical step involves a spiroannelation of the enamine of aldehyde 11 with 1-methoxy-3-buten-2-one (16) in the presence of acetic acid to give ketone 17. Reaction of 17 with methylmagnesium iodide followed by treatment of the resultant alcohol 18 with p-toluenesulfonic acid in refluxing benzene leads directly to 1 in good overall yield. As the starting material for the preparation of the cyclopentanoid aldehyde 11 was (+)-limonene the final product is optically active and thus the absolute configuration of naturally occurring (−)-acorenone (1) is established. The preparation of a number of other optically active cyclopentanoid monoterpenes (4 and 13) is also described.

A First Generation Chemoenzymatic Synthesis of (+)-Galanthamine

2010 ◽  
Vol 63 (10) ◽  
pp. 1437 ◽  
Author(s):  
Martin G. Banwell ◽  
Xinghua Ma ◽  
Ochitha P. Karunaratne ◽  
Anthony C. Willis
Keyword(s):  
Total Synthesis ◽  
First Generation ◽  
Claisen Rearrangement ◽  
Starting Material ◽  
Chemoenzymatic Synthesis ◽  
Quaternary Carbon ◽  
Enantiomerically Pure ◽  
Rearrangement Reaction

A total synthesis of (+)-galanthamine [(+)-1] has been achieved using the readily available and enantiomerically pure metabolite 2 as starting material. The quaternary carbon centre (C8a) associated with target 1 was constructed using the Eschenmoser–Claisen rearrangement reaction.

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.

Recent advances on the synthesis of the antidepressant Paroxetine

2020 ◽  
Vol 27 ◽  
Author(s):  
Joana Santos ◽  
M. Fernanda Proença ◽  
Ana Joao Rodrigues ◽  
Patricia Patrício ◽  
H. Sofia Domingues
Keyword(s):  
Total Synthesis ◽  
Neurological Disorders ◽  
Serotonin Reuptake ◽  
Potent Inhibitor ◽  
Starting Material ◽  
Substitution Pattern ◽  
Biological Probes ◽  
Recent Advances ◽  
Treatment Of Depression ◽  
Made In

: Paroxetine is a potent inhibitor of serotonin reuptake and is widely prescribed for the treatment of depression and other neurological disorders. The synthesis of paroxetine and the possibility to prepare derivatives with a specific substitution pattern that may allow their use as biological probes, is an attractive topic especially for medicinal chemists engaged in neurosciences research. Considering the extensive work that was developed in the last decade on the total synthesis of paroxetine, this review summarizes the most important contributions in this field, organized according to the reagent that was used as starting material. Most of the methods allowed to prepare paroxetine in 4-9 steps with an overall yield of 9-66%. Despite the progress made in this area, there is still room for improvement, searching for new eco-friendly and sustainable synthetic alternatives.

Chemoenzymatic Synthesis and Synthetic Application of Enantiopure Aminocyclopentenols:  Total Synthesis of Carbocyclic (+)-Uracil Polyoxin C and Its α-Epimer

2004 ◽  
Vol 69 (13) ◽  
pp. 4538-4540 ◽  
Author(s):  
Fangzheng Li ◽  
John B. Brogan ◽  
Jennifer L. Gage ◽  
Deyi Zhang ◽  
Marvin J. Miller
Keyword(s):  
Total Synthesis ◽  
Chemoenzymatic Synthesis ◽  
Synthetic Application

Total synthesis of (−)-Allosamidin, an insect chitinase inhibitor, employing chitin as a key starting material

1992 ◽  
Vol 33 (49) ◽  
pp. 7565-7568 ◽  
Author(s):  
Shunya Takahashi ◽  
Hiroyuki Terayama ◽  
Hiroyoshi Kuzuhara
Keyword(s):  
Total Synthesis ◽  
Starting Material

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.

Chemoenzymatic Synthesis and Function of Chitin Derivatives

2020 ◽  
Vol 26 (29) ◽  
pp. 3522-3529 ◽  
Author(s):  
Makoto Ogata
Keyword(s):  
Total Synthesis ◽  
Raw Materials ◽  
Functional Materials ◽  
Chemoenzymatic Synthesis ◽  
Esterification Reaction ◽  
Marine Life ◽  
Egg White Lysozyme ◽  
Hen Egg White ◽  
And Function ◽  
Effective Use

Chitin, abundant biomass found in crab shells and other marine life, has wide applications in the production of food, pharmaceuticals, and cosmetics. Our recent studies have focused on the development of new functional materials by derivatizing chitin oligosaccharides and monosaccharides. For example, we have prepared various derivatives by chemoenzymatic synthesis using N-acetylglucosamine (GlcNAc) or chitin oligosaccharide prepared from chitin as starting materials. First, we have achieved the total synthesis of two secondary metabolites (furanodictine A and B) with neuronal differentiation-inducing activity on PC12 cells by using a simple heatinduced structural transformation of GlcNAc and esterification reaction. Second, we synthesized both a novel inhibitor that has facilitated a re-examination of the reaction mechanism of hen egg-white lysozyme, and a new substrate for assaying lysozyme activity by using chitin oligosaccharides as raw materials. Thus, the development of new materials by simple derivatization of chitin mono- or oligo-saccharides is paving the way for effective use of chitin.

Synthesis of Carbocyclic Nucleosides (+)-Neplanocin A, (+)-Aristeromycin and 4'-epi-(+)-Aristeromycin from D-Fructose

2019 ◽  
Vol 16 (9) ◽  
pp. 750-758
Author(s):  
Perali R. Sridhar ◽  
Vennam D.K. Reddy ◽  
Mandava Suresh ◽  
Nadiveedhi M. Reddy ◽  
K. Shiva Kumar
Keyword(s):  
Total Synthesis ◽  
Allylic Alcohol ◽  
Starting Material ◽  
Carbocyclic Nucleosides ◽  
Ring Closing Metathesis ◽  
Neplanocin A ◽  
Oxidative Rearrangement ◽  
Key Steps

D-Fructose is used as the chiral pool starting material for the stereoselective total synthesis of (+)-neplanocin A. Zinc mediated fragmentation, ring-closing metathesis and oxidative rearrangement of cyclic tertiary allylic alcohol are used as the key steps in achieving the synthesis of key carbocylic intermediate. Further, stereoselective total synthesis of 4'-epi-(+)-aristeromycin and the conversion of (+)-neplanocin A to a mixture of (+)-aristeromycin and 4'-epi-(+)-aristeromycin are described.

Sign in / Sign up

Export Citation Format

Share Document