ChemInform Abstract: ASYMMETRIC SYNTHESES VIA HETEROCYCLIC INTERMEDIATES. IV. ASYMMETRIC SYNTHESIS S OF α-METHYLPHENYLALANINE AND ITS ANALOGS BY ALKYLATION OF 1-CHIRAL SUBSTITUTED 4-METHYL-2-IMIDAZOLIN-5-ONE

1981 ◽  
Vol 12 (25) ◽  
Author(s):  
U. SCHOELLKOPF ◽  
H.-H. HAUSBERG ◽  
M. SEGAL ◽  
U. REITER ◽  
I. HOPPE ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Syntheses

scholarly journals Concise asymmetric syntheses of novel phenanthroquinolizidines

2016 ◽  
Vol 14 (7) ◽  
pp. 2264-2271 ◽  
Author(s):  
Cintia Anton-Torrecillas ◽  
María Isabel Loza ◽  
José Brea ◽  
Jose C. Gonzalez-Gomez
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Syntheses ◽  
Quaternary Center

A concise asymmetric synthesis of cytotoxic phenanthroquinolizidines with a quaternary center at C14a and a substituent at C9 is described.

scholarly journals Asymmetric syntheses of (+)- and (–)-collybolide enable reevaluation of kappa-opioid receptor agonism

2022 ◽  
Author(s):  
Sophia Shevick ◽  
Stephan Freeman ◽  
Guanghu Tong ◽  
Robin Russo ◽  
Laura Bohn ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Opioid Receptor ◽  
Kappa Opioid Receptor ◽  
Dense Core ◽  
Fungal Metabolite ◽  
Asymmetric Syntheses ◽  
Kappa Opioid ◽  
Biased Agonist

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.

A chiral pool approach for asymmetric syntheses of (−)-antrocin, (+)-asperolide C, and (−)-trans-ozic acid

2016 ◽  
Vol 52 (84) ◽  
pp. 12426-12429 ◽  
Author(s):  
Fu-Zhuo Li ◽  
Shuang Li ◽  
Peng-Peng Zhang ◽  
Zhi-Hui Huang ◽  
Wei-Bin Zhang ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Syntheses

Ozonolysis of aromatic abietanes is used to create the important intermediates, resulting in a simple, concise, and asymmetric synthesis of three terpenes.

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