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Issue 2, 2003
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Synthesis, chiroptical properties and absolute configuration of spiro[1,3-benzodioxole-methanocyclooct[b]indole]

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Abstract

The synthesis of chiral 1′H-spiro[1,3-benzodioxole-2,12′-[6′,10′]methanocyclooct[b]indole] 3, a fused polycyclic structure derived from bicyclo[3.3.1]nonane, was accomplished via the Fisher indolization reaction. Enantiomers of this structure were obtained by chiral HPLC enantiomer separation on a swollen microcrystalline triacetylcellulose column. Chiroptical properties of the resolved enantiomers containing indole and 1,2-methylenedioxybenzene chromophores were studied. Application of the sector rule to the 1,2-methylenedioxybenzene chromophore to establish the absolute configuration of this polycyclic structure did not lead to an unequivocal conclusion which is likely to be due to the transannular interaction of the chromophores. The enantiospecific synthesis from enantiomerically enriched (−)-(1R,5S)-bicyclo[3.3.1]nonane-2,9-dione 1 was performed to prove unequivocally the (+)-(6′R,10′S)-configuration of the title structure. This study demonstrates that semiempirical rules should be applied cautiously to the determination of the absolute configuration of molecules containing several chromophores.

Graphical abstract: Synthesis, chiroptical properties and absolute configuration of spiro[1,3-benzodioxole-methanocyclooct[b]indole]

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Publication details

The article was received on 29 Aug 2002, accepted on 15 Oct 2002 and first published on 09 Dec 2002


Article type: Paper
DOI: 10.1039/B208422H
Citation: Org. Biomol. Chem., 2003,1, 391-394
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    Synthesis, chiroptical properties and absolute configuration of spiro[1,3-benzodioxole-methanocyclooct[b]indole]

    E. Butkus, J. Malinauskienė and S. Stončius, Org. Biomol. Chem., 2003, 1, 391
    DOI: 10.1039/B208422H

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