Issue 7, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Resolution and configurational assignment of 3,4,5,6-tetrahydro-2-methyl-2,6-methano-2H-1-benzoxocine derivatives

Tibor Kurtán,a   Eszter Baitz-Gács,b   Zsuzsa Májer,c   Attila Bényeid  and  Sándor Antus*a  

* Corresponding authors

a Department of Organic Chemistry, University of Debrecen, P.O.B. 20, H-4010 Debrecen, Hungary

b Institute of Chemistry, C. R. C., Hungarian Academy of Sciences, P.O.B. 32, H-1515 Budapest, Hungary

c Institute of Organic Chemistry, L. Eötvös University, H-1518 Budapest 112, P.O.B. 32, Hungary

d Department of Chemistry, Laboratory for X-Ray Diffraction, University of Debrecen, P.O.B. 7, H-4010 Debrecen, Hungary

Abstract

Chemical resolutions of the rigid, tricyclic 3,4,5,6-tetrahydro-2-methyl-2,6-methano-2H-1-benzoxocin-4-one (6) of biological and chiroptical interest have been performed. The configurational assignment was made by X-ray analysis and chemical correlation of its ketal (+)-9a synthesized with (2R,3R)-butane-2,3-diol. Kinetic resolution of the hydroxy derivative rac-10 by means of lipase from Pseudomonas cepacia proved the most effective procedure for resolution. The stereochemistry of the faster reacting enantiomer (+)-10 was deduced by chemical correlation with the ketal (+)-9. Model compounds (+)-1 and (−)-1 for chiroptical study of the chromane chromophore were also prepared.

Graphical abstract: Resolution and configurational assignment of 3,4,5,6-tetrahydro-2-methyl-2,6-methano-2H-1-benzoxocine derivatives

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Article information

DOI
https://doi.org/10.1039/B200751G
Article type
Paper
Submitted
21 Jan 2002
Accepted
13 Feb 2002
First published
08 Mar 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 888-894

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Resolution and configurational assignment of 3,4,5,6-tetrahydro-2-methyl-2,6-methano-2H-1-benzoxocine derivatives

T. Kurtán, E. Baitz-Gács, Z. Májer, A. Bényei and S. Antus, J. Chem. Soc., Perkin Trans. 1, 2002, 888 DOI: 10.1039/B200751G

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