Acid Promoted Syntheses of New Enantiopure Amino Sugar Derivatives from 3,6-Dihydro-2H-1,2-oxazines

Abstract The acid promoted rearrangement of SYN-1 with HCl led to bicyclic acetal 2 from which enantiopure furan derivative 4 was obtained by hydrogenolysis. The same sequence was applied to ANTI-1 leading to bicyclus 3 and diastereomeric tetrahydrofuran 5. Treatment of SYN-6 with pyridinium hydroge...

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Bibliographic Details
Published in:Synlett 2002, Vol.2002 (5), p.817-819
Main Authors: Pulz, Robert, Al-Harrasi, Ahmed, Reissig, Hans-Ulrich
Format: Article
Language:English
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Summary:Abstract The acid promoted rearrangement of SYN-1 with HCl led to bicyclic acetal 2 from which enantiopure furan derivative 4 was obtained by hydrogenolysis. The same sequence was applied to ANTI-1 leading to bicyclus 3 and diastereomeric tetrahydrofuran 5. Treatment of SYN-6 with pyridinium hydrogen fluoride provided either semiacetal 7 or bicyclic acetal 8, depending on the ratio of HF and pyridine. Lewis acid mediated intramolecular aldol reaction of SYN-6 afforded bicyclic 1,2-oxazine 9. Protection and subsequent stereoselective reduction of 9 led to 10, which was hydrogenated to yield enantiopure amino substituted pyran derivative 11.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2002-25361