Advantage being taken of the versatility of the siloxydiene TBSOP in asymmetric synthesis, (6S,7R,8S,8aR)-6,7,8-trihydroxyindolizidine 11 has been assembled from the L-threose derivative 1 in six or eight steps in 22-30% overall yield. Pivotal to the success of this total synthesis venture is the ready availability of unsaturated lactam 2 with complete stereocontrol. As a corollary, the synthesis of the known indolizidine enantiomer ent-11 confirms the feasibility of the procedure. The structure of compound 5 has been determined by X-ray crystallography.

Selective reactions using N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole: concise asymmetric syntheses of (+)-1-deoxy-8-epi-castanospermine and its enantiomer / Casiraghi, Giovanni; Ulgheri, Fausta; Spanu, Pietro; Rassu, Gloria; Pinna, Luigi; Fava, Giovanna Gasparri; Ferrari, Marisa Belicchi; Pelosi, Giorgio. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 23(1993), pp. 2991-2997. [10.1039/p19930002991]

Selective reactions using N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole: concise asymmetric syntheses of (+)-1-deoxy-8-epi-castanospermine and its enantiomer

PELOSI, Giorgio
1993-01-01

Abstract

Advantage being taken of the versatility of the siloxydiene TBSOP in asymmetric synthesis, (6S,7R,8S,8aR)-6,7,8-trihydroxyindolizidine 11 has been assembled from the L-threose derivative 1 in six or eight steps in 22-30% overall yield. Pivotal to the success of this total synthesis venture is the ready availability of unsaturated lactam 2 with complete stereocontrol. As a corollary, the synthesis of the known indolizidine enantiomer ent-11 confirms the feasibility of the procedure. The structure of compound 5 has been determined by X-ray crystallography.
1993
Selective reactions using N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole: concise asymmetric syntheses of (+)-1-deoxy-8-epi-castanospermine and its enantiomer / Casiraghi, Giovanni; Ulgheri, Fausta; Spanu, Pietro; Rassu, Gloria; Pinna, Luigi; Fava, Giovanna Gasparri; Ferrari, Marisa Belicchi; Pelosi, Giorgio. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 23(1993), pp. 2991-2997. [10.1039/p19930002991]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2823048
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