A Novel and Practical Synthesis of (+)-Biotin via Fukuyama Coupling Reaction

ChemInform ◽  
2003 ◽  
Vol 34 (22) ◽  
Author(s):  
Toshiaki Shimizu
Keyword(s):  
Coupling Reaction ◽  
Practical Synthesis

Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

2017 ◽  
Vol 68 (1) ◽  
pp. 180-185
Author(s):  
Adriana Maria Andreica ◽  
Lucia Gansca ◽  
Irina Ciotlaus ◽  
Ioan Oprean
Keyword(s):  
Sex Pheromone ◽  
Coupling Reaction ◽  
Coupling Scheme ◽  
Lithium Aluminium Hydride ◽  
Terminal Alkyne ◽  
Mercury Derivative ◽  
Lithium Aluminium ◽  
Convenient Synthesis ◽  
Practical Synthesis ◽  
Insect Sex

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

Ph3P-mediated highly selective C(α)–P coupling of quinone monoacetals with R2P(O)H: convenient and practical synthesis of ortho-phosphinyl phenols

2018 ◽  
Vol 20 (22) ◽  
pp. 5111-5116 ◽  
Author(s):  
Ruwei Shen ◽  
Ming Zhang ◽  
Jing Xiao ◽  
Chao Dong ◽  
Li-Biao Han
Keyword(s):  
Coupling Reaction ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Practical Synthesis

The Ph3P-mediated C(α)–P coupling reaction of quinone monoacetals with secondary phosphine oxides is developed to provide an effective method for the synthesis of a wide array of ortho-phosphinyl phenols in good to excellent yields.

scholarly journals CuI nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by SNAr-type C–S, C–N bond formation from isothiocyanatobenzenes and benzimidazoles

RSC Advances ◽  
2018 ◽  
Vol 8 (39) ◽  
pp. 22259-22267 ◽  
Author(s):  
Xiaolong Guo ◽  
Luyao Wang ◽  
Jing Hu ◽  
Mengmeng Zhang
Keyword(s):  
Bond Formation ◽  
Coupling Reaction ◽  
Type C ◽  
Practical Synthesis ◽  
Anti Hiv

We proposed a practical synthesis of analogs of the anti-HIV drug 3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine via a CuI nanoparticle-catalyzed intramolecular C(sp2)–S coupling reaction.

A Practical Synthesis of (Z)- and (E)-8-Dodecene-1-yl Acetate, Components of Lepidoptera Insect Sex Pheromones

2017 ◽  
Vol 68 (1) ◽  
pp. 157-162
Author(s):  
Irina Ciotlaus ◽  
Lucia Gansca ◽  
Adriana Maria Andreica ◽  
Ioan Oprean
Keyword(s):  
Sex Pheromones ◽  
Coupling Reaction ◽  
Coupling Scheme ◽  
Mercury Derivative ◽  
Lithium Aluminium ◽  
Isomeric Purity ◽  
Insect Sex Pheromones ◽  
Practical Synthesis ◽  
The Common ◽  
Insect Sex

New and practical synthesis of (Z)-8-dodecene-1-yl acetate and (E)-8-dodecene-1-yl acetate were developed. The synthesis were based on a C3+C6=C9 and C9+C3=C12 coupling scheme, the starting material being 2-propyn-1-ol and 1,6-hexandiol. The routes involve, as the key step, the use of the same mercury derivative of the terminal-alkyne w-functionalised as intermediate. The first coupling reaction took place between methoxyallene and Grignard reagent of 1-tert-butoxy-6-bromo-hexan obtaining 1-tert-butoxy-non-8-yne, which is transformed in di[1-tert-butoxy-non-8-yne]mercury, the common intermediate in the synthesis of the two pheromones. In order to obtain (Z)-8-dodecene-1-yl acetate and (E)-8-dodecene-1-yl acetate, the mercury derivative was directly lithiated and then alkylated with 1-bromo-propan obtaining 1-tert-butoxy-dodec-8-yne. After acetylation of 1-tert-butoxy-dodec-8-yne and stereoselective reduction in the presence of NiP-2 catalyst gave (Z)-8-dodecene-1-yl acetate with 85 % isomeric purity. After reduction with lithium aluminium hydride of 1-tert-butoxy-dodec-8-yne and acetylation was obtained (E)-8-dodecene-1-yl acetate with 90% isomeric purity.

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