Synthesis and Chiroptical Properties of Methanocycloocta[b]indoles

Autor:	Eugenius Butkus, Jule Malinauskiene, Berg U, Sandstrom J
Rok vydání:	2000
Předmět:	Indole test chemistry.chemical_classification Chiral column chromatography Crystallography Circular dichroism Ketone Microcrystalline Bicyclic molecule Chemistry Organic Chemistry Absolute configuration Enantiomer
Zdroj:	The Journal of Organic Chemistry. 65:1353-1358
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo991385a
Popis:	The synthesis of chiral methanocyclocta[b]indoles, the fused structures obtained from enantiomeric bicyclo[3.3.1]nonanones via Fisher indolization reaction, is reported. The starting optically active bicyclo[3.3.1]nonane-2,6-dione (1) was obtained by a chiral HPLC enantiomer separation on a swollen microcrystalline triacetylcellulose column and by the enzymatic resolution of the racemic dione. The circular dichroism (CD) spectra of the chiral structures 4, 5, and 7 were recorded, and the absolute configuration for the indole compounds was assigned. The theoretical calculations of the CD spectrum of diindole 4 reproduce the 1Bb couplet at 229 nm but predict wrong signs for the 1La and 1Lb bands using standard polarization directions. The CD spectrum of indole ketone 5 is reproduced correctly.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::63a510eae528f6c0846d04a0ca7bd3e0 https://doi.org/10.1021/jo991385a Zobrazit plný text záznamu