Enantiomerically pure 1,5-dideoxy-1,5-imino-D-glycero-D-allo-heptitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-D-glyceraldehyde-N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4, followed by diastereoselective anti, cis-dihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9. © 1992.
Total synthesis of 1,5-dideoxy-1,5-iminoalditols / Rassu, Gloria; Pinna, Luigi; Spanu, Pietro; Culeddu, Nicola; Casiraghi, Giovanni; Fava, Giovanna Gasparri; Ferrari, Marisa Belicchi; Pelosi, Giorgio. - In: TETRAHEDRON. - ISSN 0040-4020. - 48:4(1992), pp. 727-742. [10.1016/S0040-4020(01)88132-1]
Total synthesis of 1,5-dideoxy-1,5-iminoalditols
CASIRAGHI, Giovanni;PELOSI, Giorgio
1992-01-01
Abstract
Enantiomerically pure 1,5-dideoxy-1,5-imino-D-glycero-D-allo-heptitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-D-glyceraldehyde-N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4, followed by diastereoselective anti, cis-dihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9. © 1992.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
