A Novel Stereoselective Synthesis of cis-Configured Erythrinane and Erythrinane Type Analogues

Autor:	Christian Ettmayr, Eberhard Reimann
Rok vydání:	2004
Předmět:	Acylation Tetracyclus Chemistry Stereochemistry Intramolecular force Aromatic ketones Moiety Stereoselectivity General Medicine General Chemistry Nuclear magnetic resonance spectroscopy
Zdroj:	Monatshefte f�r Chemie/Chemical Monthly. 135
ISSN:	1434-4475 0026-9247
DOI:	10.1007/s00706-003-0158-2
Popis:	N-Alkylation of certain angularly substituted heterocycles by C2- and C3-units provided appropriate precursors to construct stereoselectively the erythrinanone and several erythrinanone type analogues by intramolecular Friedel-Crafts acylation. The resulting aromatic ketones were catalytically reduced affording the corresponding parent frameworks including the hitherto unknown tetracyclus A-norschelhammerane. On the other hand, the stereoselective reduction of the carbonyl moiety offered a convenient approach to 11-hydroxylated erythrinanes with the natural occurring β-configuration. The structures and the stereochemistry of the target compounds were proved by NMR spectroscopy.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f8bf059e1ef6dd2e74e65ca5441a02ca https://doi.org/10.1007/s00706-003-0158-2 Zobrazit plný text záznamu Full text from SpringerLink