High-Yielding Total Synthesis of Sexually Deceptive Chiloglottones and Antimicrobial Dialkylresorcinols through an Organocatalytic Reductive Coupling Reaction

2014 ◽  
Vol 2014 (33) ◽  
pp. 7317-7323 ◽  
Author(s):  
Rudrakshula Madhavachary ◽  
Dhevalapally B. Ramachary
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Reductive Coupling

scholarly journals Phosphite-Mediated Reductive Cross-Coupling of Isatins and Nitro­styrenes

Synthesis ◽  
2017 ◽  
Vol 49 (12) ◽  
pp. 2663-2676 ◽  
Author(s):  
Somayeh Motevalli ◽  
Jeffrey Johnson
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Reductive Coupling ◽  
Title Reaction ◽  
Dimethyl Phosphite ◽  
Mild Conditions ◽  
Michael Type Addition

A new reductive coupling reaction between N-alkylisatins, dimethyl phosphite, and nitrostyrenes has been developed. The reaction relies on Pudovik addition, subsequent phosphonate–phosphate rearrangement, and Michael-type addition of a transient carbanion on the indolinone with β-nitrostyrenes. This protocol introduces a convenient and versatile method for the construction of polyfunctionalized tertiary phosphates under mild conditions. Chiral general bases catalyze the title reaction with promising levels of enantioselectivity.

scholarly journals Stereocontrolled total synthesis of (+)-vinblastine

2003 ◽  
Vol 75 (1) ◽  
pp. 29-38 ◽  
Author(s):  
Satoshi Yokoshima ◽  
T. Ueda ◽  
S. Kobayashi ◽  
A. Sato ◽  
Takeshi Kuboyama ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Radical Cyclization ◽  
Critical Coupling ◽  
Efficient Manner ◽  
Complete Control ◽  
Highly Efficient ◽  
Indole Synthesis

Stereocontrolled total synthesis of (+)-vinblastine (1) has been achieved using a novel radical-mediated indole synthesis developed in our laboratories. The isothiocyanate 18, prepared readily from quinoline 17, underwent a facile addition of the malonate anion to give 19. The o-alkenylthioanilide 19 was then converted to indole 20 by radical cyclization and protection. (−)-Vindoline (2) was prepared from this key intermediate 20 in a highly efficient manner. The indole core of the 11-membered intermediate 3 was constructed similarly from quinoline. The critical coupling reaction between 2 and the chloroindolenine derived from 3 proceeded with complete control of stereochemistry to give the desired product 66 in 97 % yield, which could be successfully converted to (+)-vinblastine (1).

The role of oligomers in the synthesis of polysilanes by the Wurtz reductive coupling reaction

2003 ◽  
Vol 685 (1-2) ◽  
pp. 60-64 ◽  
Author(s):  
Daniel Bratton ◽  
Simon J. Holder ◽  
Richard G. Jones ◽  
William K.C. Wong
Keyword(s):  
Coupling Reaction ◽  
Reductive Coupling

THE REDUCTIVE COUPLING REACTION OF DIARYLIODONIUM SALTS CATALYZED BY PALLADIUM–ZINC SYSTEM

1983 ◽  
Vol 12 (8) ◽  
pp. 1165-1166 ◽  
Author(s):  
Masaharu Uchiyama ◽  
Takehiko Suzuki ◽  
Yasuo Yamazaki
Keyword(s):  
Coupling Reaction ◽  
Reductive Coupling ◽  
Diaryliodonium Salts

scholarly journals Synthetic Approach toward α-Aminomethyl-γ-butyrolactones from β-Lactam Synthons Elaborated by SmI2-mediated Reductive Coupling Reactions

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800
Author(s):  
Masaki Takahashi ◽  
Takahiro Sudo ◽  
Yusuke Murata ◽  
Tetsuya Sengoku ◽  
Hidemi Yoda
Keyword(s):  
Ring Opening ◽  
Coupling Reaction ◽  
Synthetic Approach ◽  
Coupling Reactions ◽  
Reductive Coupling ◽  
Important Class

A simple and straightforward synthetic approach was developed to access a biologically important class of α-aminomethyl-γ-butyrolactones via a β-lactam synthon strategy involving successive ring-opening and lactonization processes from α-hydroxyethyl-substituted β-lactams that were elaborated by SmI2-mediated reductive coupling reaction.

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