CuLi2Cl4 Catalyzed Cross-coupling Strategy for the Formal Synthesis of (+)-Subersic Acid from (-)-Sclareol_esi

2017 ◽  
Keyword(s):  
Cross Coupling ◽  
Formal Synthesis ◽  
Coupling Strategy

CuLi2Cl4 catalysed cross-coupling strategy for the formal synthesis of the diterpenoid (+)-subersic acid from (–)-sclareol

2017 ◽  
Vol 41 (7) ◽  
pp. 394-397 ◽  
Author(s):  
Qiangyong Wu ◽  
Peiqiang Wang ◽  
Bin Zhou ◽  
Sikai Hua ◽  
Jiangmeng Ren ◽  
...  
Keyword(s):  
Functional Group ◽  
Cross Coupling ◽  
Hydroxybenzoic Acid ◽  
Formal Synthesis ◽  
Coupling Strategy

A CuLi2Cl4-catalysed regioselective cross-coupling is used in a key step leading to the concise synthesis of (+)-subersic acid with an overall yield of 25.7% from commercially available (–)-sclareol. The coupled product 15-(2-methoxy-5-carbomethoxy)phenyl-labda-8(9),13 E-diene was obtained in 62% yield under CuLi2Cl4 conditions starting from 2-iodo-4-carbomethoxyanisole and 15-acetoxy-labda-8(9),13 E-diene. These were derived from 4-hydroxybenzoic acid and (–)-sclareol respectively. The 15-(2-methoxy-5-carbomethoxy)phenyl-labda-8(9),13 E-diene was easily transformed into (+)-subersic acid by demethylation of the phenol ether and ester. This cross-coupling strategy showed a good functional group tolerance and various (+)-subersic acid derivatives were obtained in moderate yields.

A biaryl cross-coupling strategy for functionalisation of benzocrown ethers

2007 ◽  
pp. 3565 ◽  
Author(s):  
Sally Dixon ◽  
Richard C. D. Brown ◽  
Philip A. Gale
Keyword(s):  
Cross Coupling ◽  
Benzocrown Ethers ◽  
Coupling Strategy

Electrochemical and direct C–H methylthiolation of electron-rich aromatics

2020 ◽  
Vol 22 (15) ◽  
pp. 4906-4911
Author(s):  
Yaxing Wu ◽  
Hongliang Ding ◽  
Ming Zhao ◽  
Zhong-Hai Ni ◽  
Jing-Pei Cao
Keyword(s):  
Cross Coupling ◽  
Coupling Strategy

The electrochemical-induced C–H methylthiolation of electron-rich aromatics has been accomplished via a three component cross-coupling strategy.

scholarly journals Double Heck Route to a Dibenzoxepine and Convergent Suzuki Cross-Coupling Strategy for the Synthesis of an MR Antagonist

2017 ◽  
Vol 21 (2) ◽  
pp. 208-217 ◽  
Author(s):  
Marvin M. Hansen ◽  
Neil J. Kallman ◽  
Thomas M. Koenig ◽  
Ryan J. Linder ◽  
Rachel N. Richey ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Strategy

Synthesis of new pyridine intermediates as precursors for the elaboration of streptonigrin analogues by the metalation-cross-coupling strategy

1996 ◽  
Vol 33 (6) ◽  
pp. 1995-2005 ◽  
Author(s):  
V. Pomel ◽  
J. C. Rovera ◽  
A. Godard ◽  
F. Marsais ◽  
G. Quéguiner
Keyword(s):  
Cross Coupling ◽  
Coupling Strategy

Practical, Modular, and General Synthesis of Benzofurans through Extended Pummerer Annulation/Cross-Coupling Strategy

2014 ◽  
Vol 126 (29) ◽  
pp. 7640-7643 ◽  
Author(s):  
Kei Murakami ◽  
Hideki Yorimitsu ◽  
Atsuhiro Osuka
Keyword(s):  
Cross Coupling ◽  
Coupling Strategy ◽  
General Synthesis

ChemInform Abstract: Construction of Functionalized/Substituted Bipyridines by Means of Negishi Cross-Coupling Reactions. Formal Synthesis of (.+-.)-Cytisine.

ChemInform ◽  
2010 ◽  
Vol 33 (3) ◽  
pp. no-no
Author(s):  
Prosper Nshimyumukiza ◽  
Dominique Cahard ◽  
Jacques Rouden ◽  
Marie-Claire Lasne ◽  
Jean-Christophe Plaquevent
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Formal Synthesis ◽  
Cross Coupling Reactions
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