Side-Chain Truncation of Apicularen A by Olefin Cross-Metathesis with Ethylene

2007 ◽  
Vol 70 (8) ◽  
pp. 1377-1379 ◽  
Author(s):  
Larissa Jundt ◽  
Gerhard Höfle
Keyword(s):  
Side Chain ◽  
Cross Metathesis ◽  
Apicularen A

scholarly journals Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid

2018 ◽  
Vol 14 ◽  
pp. 2737-2744 ◽  
Author(s):  
Jacqueline Pollini ◽  
Valentina Bragoni ◽  
Lukas J Gooßen
Keyword(s):  
First Generation ◽  
Anacardic Acid ◽  
Side Chain ◽  
Tyrosinase Inhibitor ◽  
Target Compound ◽  
Selective Precipitation ◽  
Acid Component ◽  
Cross Metathesis ◽  
Cashew Nutshell Liquid ◽  
Bond Isomers

A convenient and sustainable three-step synthesis of the tyrosinase inhibitor 2-hydroxy-6-tridecylbenzoic acid was developed that starts directly from the anacardic acid component of natural cashew nutshell liquid (CNSL). Natural CNSL contains 60–70% of anacardic acid as a mixture of several double bond isomers. The anacardic acid component was converted into a uniform starting material by ethenolysis of the entire mixture and subsequent selective precipitation of 6-(ω-nonenyl)salicylic acid from cold pentane. The olefinic side chain of this intermediate was elongated by its cross-metathesis with 1-hexene using a first generation Hoveyda–Grubbs catalyst, which was reused as precatalyst in a subsequent hydrogenation step. Overall, the target compound was obtained in an overall yield of 61% based on the unsaturated anacardic acid content and 34% based on the crude CNSL.

Synthesis of side chain truncated apicularen A

2000 ◽  
Vol 41 (42) ◽  
pp. 8069-8073 ◽  
Author(s):  
Ashoke Bhattacharjee ◽  
Jef K De Brabander
Keyword(s):  
Side Chain ◽  
Apicularen A

Side-Chain Modification and “Grafting Onto” via Olefin Cross-Metathesis

2012 ◽  
Vol 33 (23) ◽  
pp. 2023-2028 ◽  
Author(s):  
Lucas Montero de Espinosa ◽  
Kristian Kempe ◽  
Ulrich S. Schubert ◽  
Richard Hoogenboom ◽  
Michael A. R. Meier
Keyword(s):  
Side Chain ◽  
Cross Metathesis ◽  
Grafting Onto

scholarly journals 4-[(E)-4-Hydroxybut-2-en-1-yl]-2-methoxyphenol

IUCrData ◽  
2016 ◽  
Vol 1 (6) ◽  
Author(s):  
Kyle S. Knight ◽  
Michael C. Orick
Keyword(s):  
Hydrogen Bonds ◽  
Aromatic Ring ◽  
Dihedral Angle ◽  
Title Compound ◽  
Side Chain ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Compound C

The title compound, C11H14O3, was synthesized by a cross-metathesis reaction. The dihedral angle between the aromatic ring and the butenol side chain is 30.2 (2)°. In the crystal, inversion dimers are formed through O—H...O hydrogen bonds and these are linked into chains by additional O—H...O contacts. These chains are linked into sheets in thebcplane by C—H...O hydrogen bonds.

scholarly journals Synthesis and Glycosidase Inhibition of Broussonetine M and Its Analogues

Molecules ◽  
2019 ◽  
Vol 24 (20) ◽  
pp. 3712 ◽  
Author(s):  
Wu ◽  
Kinami ◽  
Kato ◽  
Li ◽  
Fleet ◽  
...  
Keyword(s):  
Natural Product ◽  
Hydroxyl Group ◽  
Side Chain ◽  
Alkyl Side Chain ◽  
Asymmetric Allylation ◽  
Pyrrolidine Ring ◽  
Cross Metathesis ◽  
Similar Strategy ◽  
Key Steps ◽  
Glycosidase Inhibition

Cross-metathesis (CM) and Keck asymmetric allylation, which allows access to defined stereochemistry of a remote side chain hydroxyl group, are the key steps in a versatile synthesis of broussonetine M (3) from the d-arabinose-derived cyclic nitrone 14. By a similar strategy, ent-broussonetine M (ent-3) and six other stereoisomers have been synthesized, respectively, starting from l-arabino-nitrone (ent-14), l-lyxo-nitrone (ent-3-epi-14), and l-xylo-nitrone (2-epi-14) in five steps, in 26%–31% overall yield. The natural product broussonetine M (3) and 10’-epi-3 were potent inhibitors of β-glucosidase (IC50 = 6.3 μM and 0.8 μM, respectively) and β-galactosidase (IC50 = 2.3 μM and 0.2 μM, respectively); while their enantiomers, ent-3 and ent-10’-epi-3, were selective and potent inhibitors of rice α-glucosidase (IC50 = 1.2 μM and 1.3 μM, respectively) and rat intestinal maltase (IC50 = 0.29 μM and 18 μM, respectively). Both the configuration of the polyhydroxylated pyrrolidine ring and C-10’ hydroxyl on the alkyl side chain affect the specificity and potency of glycosidase inhibition.

ChemInform Abstract: Synthesis of Side Chain Truncated Apicularen A.

ChemInform ◽  
2001 ◽  
Vol 32 (2) ◽  
pp. no-no
Author(s):  
Ashoke Bhattacharjee ◽  
Jef K. De Brabander
Keyword(s):  
Side Chain ◽  
Apicularen A

Electroluminescent properties of side-chain naphthalimide-derivated polymers

1998 ◽  
Vol 95 (6) ◽  
pp. 1351-1354 ◽  
Author(s):  
C.-M. Bouché ◽  
P. Le Barny ◽  
H. Facoetti ◽  
F. Soyer ◽  
P. Robin
Keyword(s):  
Side Chain
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