A novel route to the hexacyclic indole alkaloid cuanzine 1 has been developed. Key synthetic steps include the cyclocondensation of the imine 8 with the dihydrofuran 10 followed by homogeneous-catalyzed hydrogenation, wherein the COOMe group at C(20) serves as a diastereocontrol element in establishing the C(15) stereogenicity. In order to define local energy minima, the conformational space of some intermediates has been explored by empirical force field calculations (MM2).
HEXACYCLIC INDOLE ALKALOIDS - A HIGHLY CONVERGENT TOTAL SYNTHESIS OF CUANZINE / G. PALMISANO, B. DANIELI, G. LESMA, D. PASSARELLA, L. TOMA. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 56:7(1991), pp. 2380-2386. [10.1021/jo00007a024]
HEXACYCLIC INDOLE ALKALOIDS - A HIGHLY CONVERGENT TOTAL SYNTHESIS OF CUANZINE
B. DanieliSecondo
;G. Lesma;D. PassarellaPenultimo
;
1991
Abstract
A novel route to the hexacyclic indole alkaloid cuanzine 1 has been developed. Key synthetic steps include the cyclocondensation of the imine 8 with the dihydrofuran 10 followed by homogeneous-catalyzed hydrogenation, wherein the COOMe group at C(20) serves as a diastereocontrol element in establishing the C(15) stereogenicity. In order to define local energy minima, the conformational space of some intermediates has been explored by empirical force field calculations (MM2).
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