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. DANIELI
Secondo
;
G. LESMA
Penultimo
;
D. PASSARELLA
Ultimo
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.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/183733
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