Concise syntheses of two enantiomeric tetrahydroxyquinolizidines, 10 and ent-10, have been achieved from D-arabinose and L-arabinose, respectively. Highly diastereoselective homologation of imine 5 (or ent-5) using 2-(trimethylsiloxy)furan provided the nine-carbon butenolide 6 (or ent-6) which was elaborated into the quinolizidine 10 (or ent-10) via a clean sequence involving, as key operations, DBU-promoted γ-lactone to δ-lactam ring expansion (e.g. 7 to 8) and cyclodehydration of a fully-deprotected hydroxypiperidine employing Ph3P, CCl4, Et3N (e.g. 9 to 10). The procedure comprises five steps from 5 or ent-5 and provides the title quinolizidine 10 or its enantiomer ent-10 in 36-37% overall yields. © 1993.
Efficient total syntheses of (1R, 2R, 3R, 9R, 9aR)-1,2,3,9-tetrahydroxyquinolizidine and its enantiomer / Rassu, G.; Casiraghi, G.; Pinna, L.; Spanu, P.; Ulgheri, F.; Cornia, M.; Zanardi, F.. - In: TETRAHEDRON. - ISSN 0040-4020. - 49:30(1993), pp. 6627-6636. [10.1016/S0040-4020(01)81832-9]
Efficient total syntheses of (1R, 2R, 3R, 9R, 9aR)-1,2,3,9-tetrahydroxyquinolizidine and its enantiomer
Casiraghi G.;Cornia M.;
1993-01-01
Abstract
Concise syntheses of two enantiomeric tetrahydroxyquinolizidines, 10 and ent-10, have been achieved from D-arabinose and L-arabinose, respectively. Highly diastereoselective homologation of imine 5 (or ent-5) using 2-(trimethylsiloxy)furan provided the nine-carbon butenolide 6 (or ent-6) which was elaborated into the quinolizidine 10 (or ent-10) via a clean sequence involving, as key operations, DBU-promoted γ-lactone to δ-lactam ring expansion (e.g. 7 to 8) and cyclodehydration of a fully-deprotected hydroxypiperidine employing Ph3P, CCl4, Et3N (e.g. 9 to 10). The procedure comprises five steps from 5 or ent-5 and provides the title quinolizidine 10 or its enantiomer ent-10 in 36-37% overall yields. © 1993.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
