Issue 3, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis and circular dichroism of steroids with 2,3-dihydro-1-benzofuran and 4H-benzopyranchromophores; revision of the absolute configuration of some norneolignans from Krameria cystisoides

Tibor Kurtán,a   Eszter Baitz-Gács,b   Zsuzsa Majerc  and  Sándor Antus*a  

* Corresponding authors

a Department of Organic Chemistry, Lajos Kossuth University, P.O.B. 20, Debrecen, Hungary

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

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

Abstract

Starting from cholesterol the 2,3-dihydrobenzo[b]furans 12a, 12b, and the 4H-benzopyran derivative 14 with known absolute conformation were synthesized by a stereocontrolled sequence. The same helicity rule was found to be valid for both chromophores; the P/M helicity of the heteroring leads to a negative/positive CD within the α-band. On the basis of this rule the absolute configuration of norneolignans 24–26 isolated from Krameria cystisoides was also revised.

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Article information

DOI
https://doi.org/10.1039/A905697A
Article type
Paper
Submitted
14 Jul 1999
Accepted
03 Nov 1999
First published
26 Jan 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 453-461

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Synthesis and circular dichroism of steroids with 2,3-dihydro-1-benzofuran and 4H-benzopyran chromophores; revision of the absolute configuration of some norneolignans from Krameria cystisoides

T. Kurtán, E. Baitz-Gács, Z. Majer and S. Antus, J. Chem. Soc., Perkin Trans. 1, 2000, 453 DOI: 10.1039/A905697A

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