asymmetric synthesis
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2022 ◽  
Sophia Shevick ◽  
Stephan Freeman ◽  
Guanghu Tong ◽  
Robin Russo ◽  
Laura Bohn ◽  

The fungal metabolite collybolide attracted attention as a non-nitrogenous, potent and biased agonist of the kappa-opioid receptor (KOR). Here we report a 10-step asymmetric synthesis of this complex sesquiterpene that enables facile access to either enantiomer. The synthesis relies on a diastereoselective α-benzoyloxylation to install the buried C6 benzoate and avoid irreversible translactonization of the congested, functionally dense core. Neither enantiomer, however, exhibited KOR agonism, indicating that collybolide has been mischaracterized as a KOR agonist and leaving open the basis for antipruritic effects in mice.

2022 ◽  
pp. 593-654
Béla Török ◽  
Christian Schäfer ◽  
Anne Kokel

2022 ◽  
Luo Ge ◽  
Syuzanna R Harutyunyan

Chiral bisphosphine ligands are of key importance in transition-metal-catalyzed asymmetric synthesis of optically active products. However, the transition metals typically used are scarce and expensive noble metals, while the synthetic routes...

2022 ◽  
Jiawen Lang ◽  
Siyuan Wang ◽  
Changli He ◽  
Xiaohua Liu ◽  
Xiaoming Feng

An efficient asymmetric synthesis of isochromanone derivatives was realized through Z-selective-1,3-OH insertion/aldol cyclization reaction involving acyclic carboxylic oxonium ylides. The combination of achiral dirhodium salts and chiral N,N’-dioxide-metal complexes, along...

Xiang-Hong He ◽  
Xue-Ju Fu ◽  
Gu Zhan ◽  
Nan Zhang ◽  
Xiang Li ◽  

Organocatalytic asymmetric [3 + 3] annulations of isatin-derived MBH carbonates and indolin-2-imines have been efficiently achieved. This appears to be the first enantioselective approach to use isatin-derived MBH carbonates as...

Tong-Hao Li ◽  
Da-Ming Du

A highly efficient squaramide‐catalysed asymmetric domino Michael/Mannich [3 + 2] cycloaddition of 3‐methyl‐4‐nitro‐5‐ isatylidenyl‐isoxazoles and N‐2,2,2‐trifluoroethylisatin ketimines was developed. A new class of complex and skeletondiversified isoxazole and trifluoromethyl‐containing 3,2’‐pyrrolidinyl...

2022 ◽  
Naoki Yasukawa ◽  
Ami Yamanoue ◽  
Tsunayoshi Takehara ◽  
Takeyuki Suzuki ◽  
Shuichi Nakamura

The first enantioselective aza-Henry reaction of non-activated cyclic iminoesters, derived from cyclic amino acids, has been developed. Good yields and enantioselectivities were observed for the reaction using our original cinchona...

Shiqi Jia ◽  
Wenling Qin ◽  
Pengfei Wang ◽  
Hailong Yan

An organocatalytic methodology toward the atroposelective construction of axially chiral nonsymmetric biaryltriols has been successfully developed. Quinine-derived thiourea-catalyzed intramolecular reaction through VQM (vinylidene ortho-quinone methides) intermediate enabled efficient access to...

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