An efficient synthesis of the cuanzine precursor 4d has been achieved beginning with 8-methoxy-dihydro-β-carboline 3b and utilizing as the key step the stereocontrolled alkylation of 16a (and/or 20a) followed by Hg(II)-induced heterocyclization. The structure and stereochemistry of 4d are thereby corroborated by chemical correlation with natural cuanzine 1a.
SYNTHETIC STUDIES ON INDOLE ALKALOIDS - A STEREOCONTROLLED ENTRY TO THE CUANZINE STRUCTURAL UNIT / G. PALMISANO, B. DANIELI, G. LESMA, D. PASSARELLA. - In: TETRAHEDRON. - ISSN 0040-4020. - 45:11(1989), pp. 3583-3596.
SYNTHETIC STUDIES ON INDOLE ALKALOIDS - A STEREOCONTROLLED ENTRY TO THE CUANZINE STRUCTURAL UNIT
B. DANIELISecondo
;G. LESMAPenultimo
;D. PASSARELLAUltimo
1989
Abstract
An efficient synthesis of the cuanzine precursor 4d has been achieved beginning with 8-methoxy-dihydro-β-carboline 3b and utilizing as the key step the stereocontrolled alkylation of 16a (and/or 20a) followed by Hg(II)-induced heterocyclization. The structure and stereochemistry of 4d are thereby corroborated by chemical correlation with natural cuanzine 1a.
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