An efficient alternative to the total synthesis of isophytol

2021 ◽  
Vol 18 ◽  
Author(s):  
Thirupathi Reddy Yerramreddy ◽  
Alexandros Yiannikouris
Keyword(s):  
Total Synthesis ◽  
Tertiary Alcohol ◽  
Synthetic Methods ◽  
High Yield ◽  
Alternative Method ◽  
Efficient Alternative ◽  
Viable Approach

: An improved and alternative method for the total synthesis of isophytol from citral via using pseudoionone intermediate was developed and described in this manuscript. This alternative commercially viable approach involved six steps and represents an alternative commercially viable over existing published synthetic methods in the literature. This goal was achieved by developing and optimizing an efficient and high yield procedure for the synthesis of a key intermediate i.e., 6,10,14 trimethylpentadectrimethylpentadec-5-en-2-one by reacting 2-methoxypropene with a tertiary alcohol (3,7,11 trimethyldodec-1-ene-3-ol). Isophytol was provided in 58-60% overall yield from citral with >99% purity, evaluated by TLC, GC, and NMR.

scholarly journals General, Divergent Platform for Diastereoselective Synthesis of trans-Cyclooctenes with High Reactivity and Favorable Physiochemical Properties

2021 ◽  
Author(s):  
Jessica E. Pigga ◽  
Julia Rosenberger ◽  
Andrew Jemas ◽  
Samantha Boyd ◽  
Olga Dmitrenko ◽  
...  
Keyword(s):  
Physicochemical Properties ◽  
Large Scale ◽  
High Reactivity ◽  
Diels Alder ◽  
Synthetic Methods ◽  
High Yield ◽  
Physiochemical Properties ◽  
New Class ◽  
State Models

<p><i>trans</i>-Cyclooctenes (TCOs) are essential partners for the fastest known bioorthogonal reactions, but current synthetic methods are limited by poor diastereoselectivity. Especially hard to access are hydrophilic TCOs with favorable physicochemical properties for live cell or <i>in vivo </i>experiments. Described is a new class of TCOs, ‘a-TCOs’, that is prepared in high yield via stereocontrolled 1,2-additions of nucleophiles to trans-cyclooct-4-enone, which itself was prepared on large scale in two steps from 1,5-cyclooctadiene. Computational transition state models rationalize the diastereoselectivity of 1,2-additions to deliver a-TCO products, which were also shown to be more reactive than standard TCOs and less hydrophobic than even a <i>trans</i>-oxocene analog. Illustrating the favorable physicochemical properties of a-TCOs, a fluorescent TAMRA derivative in live HeLa cells was shown to be cell-permeable through intracellular Diels-Alder chemistry and to washout more rapidly than other TCOs.</p>

scholarly journals General, Divergent Platform for Diastereoselective Synthesis of trans-Cyclooctenes with High Reactivity and Favorable Physiochemical Properties

2021 ◽  
Author(s):  
Jessica E. Pigga ◽  
Julia Rosenberger ◽  
Andrew Jemas ◽  
Samantha Boyd ◽  
Olga Dmitrenko ◽  
...  
Keyword(s):  
Physicochemical Properties ◽  
Large Scale ◽  
High Reactivity ◽  
Diels Alder ◽  
Synthetic Methods ◽  
High Yield ◽  
Physiochemical Properties ◽  
New Class ◽  
State Models

<p><i>trans</i>-Cyclooctenes (TCOs) are essential partners for the fastest known bioorthogonal reactions, but current synthetic methods are limited by poor diastereoselectivity. Especially hard to access are hydrophilic TCOs with favorable physicochemical properties for live cell or <i>in vivo </i>experiments. Described is a new class of TCOs, ‘a-TCOs’, that is prepared in high yield via stereocontrolled 1,2-additions of nucleophiles to trans-cyclooct-4-enone, which itself was prepared on large scale in two steps from 1,5-cyclooctadiene. Computational transition state models rationalize the diastereoselectivity of 1,2-additions to deliver a-TCO products, which were also shown to be more reactive than standard TCOs and less hydrophobic than even a <i>trans</i>-oxocene analog. Illustrating the favorable physicochemical properties of a-TCOs, a fluorescent TAMRA derivative in live HeLa cells was shown to be cell-permeable through intracellular Diels-Alder chemistry and to washout more rapidly than other TCOs.</p>

A new one-pot synthesis of μ-oxo dimeric iron(III) porphyrins from meso-tetraarylporphyrins

2009 ◽  
Vol 13 (08n09) ◽  
pp. 854-858 ◽  
Author(s):  
Qiang Liu ◽  
Yan-Zhi Gong ◽  
Chang-Jun Gong ◽  
Qing-Hong Li ◽  
Can-Cheng Guo
Keyword(s):  
Synthetic Methods ◽  
High Yield ◽  
Reaction Intermediates ◽  
Ferrous Chloride ◽  
Iron Porphyrins ◽  
One Pot ◽  
Convenient Procedure ◽  
One Pot Synthesis ◽  
New Synthesis ◽  
The One

A new synthesis of μ-oxo dimeric iron(III) porphyrins from meso-tetraarylporphyrins in one-pot procedure is reported. μ-oxo dimeric iron(III) porphyrin was obtained in high yield (up to 93%) from the reaction of meso-tetraarylporphyrin with ferrous chloride in DMF at pH 8–11. Compared with other synthetic methods of μ-oxo dimeric iron(III) porphyrin from meso-tetraarylporphyrins, the one-pot procedure has higher yields of μ-oxo dimeric iron(III) porphyrins and is a simpler and more convenient procedure. In order to evaluate the range of applicability of this method, μ-oxo dimeric iron(III) porphyrins with different substituents were prepared by the reaction of the corresponding meso-tetraarylporphyrins with ferrous chloride. The results showed that it was possible to apply this one-pot procedure to the synthesis of other μ-oxo dimeric iron porphyrins in excellent yields. A mechanism for the formation of μ-oxo dimeric iron porphyrins was proposed based on the reaction intermediates characterized by HPLC and UV-vis methods.

Diversity-Oriented Synthesis of Natural Products via Gold-Catalyzed Cascade Reactions

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1552-1571 ◽  
Author(s):  
Jianxian Gong ◽  
Zhen Yang ◽  
Yueqing Gu ◽  
Ceheng Tan
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Biologically Active ◽  
Synthetic Methods ◽  
Left Wing ◽  
Asymmetric Total Synthesis ◽  
Diversity Oriented Synthesis ◽  
Active Natural

This account describes our group’s latest research in the field of diversity-oriented synthesis of natural products via gold-catalyzed cascade reactions. We present two general strategies based on gold-catalyzed cycloisomerization: a gold-catalyzed cascade reaction of 1,7-diynes and a pinacol-terminated gold-catalyzed cascade reaction. We highlight our development of synthetic methods for the construction of biologically active natural products by using these two strategies.1 Introduction2 Gold-Catalyzed Cascade Reactions of 1,7-Diynes2.1 Collective Synthesis of C15 Oxygenated Drimane-Type Sesquiterpenoids2.2 Synthesis of Left-Wing Fragment of Azadirachtin I2.3 Collective Synthesis of Cladiellins3 Pinacol-Terminated Gold-Catalyzed Cascade Reaction3.1 Asymmetric Formal Total Synthesis of (+)-Cortistatins3.2 Total Synthesis of Orientalol F3.3 Asymmetric Total Synthesis of (–)-Farnesiferol C4 Summary and Outlook

Monomethyl β-Methylglutarate of New Synthetic Methods

2014 ◽  
Vol 960-961 ◽  
pp. 134-137
Author(s):  
Feng Wei He ◽  
Tong Liu ◽  
Ya Qin Zhang
Keyword(s):  
Sodium Hydroxide ◽  
Ethyl Ester ◽  
Acid Ester ◽  
Glutaric Acid ◽  
Addition Reaction ◽  
Tricarboxylic Acid ◽  
Synthetic Methods ◽  
High Yield

Malonate ethyl ester of butene in the presence of sodium hydroxide was synthesized by addition reaction of 2-methyl propane-1,1,3 tricarboxylic acid ester, by hydrolysis decarboxylation heatingβ-methyl glutaric acid. First with excess of methanol into methyl metaplasiaβ-methyl dimethyl glutarate, and then itsβ-methyl glutaric acid methylation, get high yield of monomethyl β-methylglutarate.

scholarly journals Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens

2018 ◽  
Vol 16 (22) ◽  
pp. 4076-4080 ◽  
Author(s):  
Hai Yu ◽  
Abhishek Santra ◽  
Yanhong Li ◽  
John B. McArthur ◽  
Tamashree Ghosh ◽  
...  
Keyword(s):  
Total Synthesis ◽  
High Yield ◽  
One Pot ◽  
Highly Efficient ◽  
Cancer Antigens

Highly efficient streamlined total synthesis of complex prioritized gangliosides was achieved chemoenzymatically by sequential one-pot multienzyme (OPME) reactions with facile C18 cartridge purification schemes followed by high-yield acylation.

The First Total Synthesis of Galloyl Tyramine

2009 ◽  
Vol 64 (4) ◽  
pp. 464-466 ◽  
Author(s):  
Nisar Ullah
Keyword(s):  
Total Synthesis ◽  
High Yield ◽  
Reaction Sequence

The first total synthesis of galloyl tyramine, an inhibitor of Pim2 kinase was accomplished in an overall high-yield reaction sequence

BCl3 Catalyzed, Solvent Free Protocol For The Synthesis Of Dihydropyrano[3,2-b]chromenediones

2020 ◽  
Vol 17 ◽  
Author(s):  
Vikas B Suryawanshi ◽  
Kalimoddin I Momin ◽  
Jairaj K Dawle ◽  
Sushil R Mathapati
Keyword(s):  
Kojic Acid ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Simple Reaction ◽  
Alternative Method ◽  
Short Period ◽  
Efficient Alternative ◽  
High Yields ◽  
Solvent Free Synthesis

: Solvent free synthesis of dihydropyrano[3,2-b]chromenediones was formulated via multi-component reactions of kojic acid, dimedone and several substituted aromatic aldehydes catalyzed with BCl3. Reactions progressed efficiently and the corresponding heterocyclic products were obtained in good to high yields within short period. The developed protocol is one of the better and efficient alternative method for synthesis of dihydropyrano[3,2-b]chromenediones. The simple reaction procedure, easy separation of products, radially available catalyst are certain benefits of this reported protocol.

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