scholarly journals Front Cover: The Hydroxylated, Tetracyclic Bisquinolizidine Alkaloids Baptifoline and Epibaptifoline: Enantioselective Synthesis and Unambiguous Assignment of their Configuration at C-13 (Eur. J. Org. Chem. 5/2019)

2019 ◽  
Vol 2019 (5) ◽  
pp. 862-862
Author(s):  
Jessica Goller ◽  
Christian B. Hübschle ◽  
Matthias Breuning
Keyword(s):  
Enantioselective Synthesis ◽  
Front Cover ◽  
Unambiguous Assignment

scholarly journals Enantioselective Synthesis of the Bisabolane Sesquiterpene (+)-1-Hydroxy-1,3,5-Bisabolatrien-10-one and Revision of its Absolute Configuration

2012 ◽  
Vol 7 (4) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Stefano Serra
Keyword(s):  
Absolute Configuration ◽  
Optical Rotation ◽  
Enantioselective Synthesis ◽  
Positive Sign ◽  
Chiral Building Block ◽  
Chemical Purity ◽  
Unambiguous Assignment ◽  
Biocatalytic Process ◽  
Good Agreement ◽  
Methyl Phenyl

The enantioselective synthesis of ( S)-1-hydroxy-1,3,5-bisabolatrien-10-one 1 is here described. This sesquiterpene was prepared using ( S)-3-(2-methoxy-4-methyl-phenyl)butan-1-ol as a chiral building block. Two different pathways were employed and both turned out to be high yielding, affording 1 in good chemical purity and without any racemization of the existing stereocenter. The spectroscopic data of the synthetic ( S)-1 were in very good agreement with those reported for the natural compound, which was extracted from Juniperus formosana heartwood and from the leaves of J. chinensis. The positive sign of the measured optical rotation value of synthetic ( S)-1 allows the unambiguous assignment of the absolute configuration of (+)-1 as the ( S)-enantiomer. This finding corrects the previous configuration determination which indicated the opposite result. At last, since even ( R)-3-(2-methoxy-4-methyl-phenyl)butan-1-ol is preparable in high enantiomer purity by mean of a different biocatalytic process, the formal synthesis of natural ( R)-1 was also accomplished.

scholarly journals Front Cover: A Straightforward Sequential Approach for the Enantioselective Synthesis of Optically Active α-Arylmethanol-1,2,3-Triazoles (Eur. J. Org. Chem. 40/2018)

2018 ◽  
Vol 2018 (40) ◽  
pp. 5464-5464
Author(s):  
Floyd C. D. Andrade ◽  
Lucas V. B. L. Pugnal ◽  
Hugo L. I. Betim ◽  
Jéssica F. Vani ◽  
Julio Zukerman-Schpector ◽  
...  
Keyword(s):  
Optically Active ◽  
Enantioselective Synthesis ◽  
Sequential Approach ◽  
Front Cover
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