Efficient Synthesis of Tetrahydroxylated Pyrrolizidines by Nitrone Cycloaddition Leading to Unnatural Stereoisomers of 7-Deoxycasuarine

A convenient and efficient method has been used for the synthesis of ten new tetrahydroxylated pyrrolizidines 12a, b, 13a-c, 14a, b, and 15a-c starting from sugar-derived cyclic nitrones prepared from D-xylose, D-arabinose, D-ribose, and L-arabinose, through a five-step reaction sequence. Pyrrolizid...

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Bibliographic Details
Published inSynlett no. 12; pp. 1668 - 1672
Main Authors Podolan, Gabriel, Klescikova, Lucia, Fisera, Lubor, Kozfsek, Jozef, Fronc, Marek
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.07.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,3-DIPOLAR CYCLOADDITIONS
CYCLIC NITRONES
INDOLIZIDINE
EN-ROUTE
CHIRAL NITRONES
sugar-derived cyclic nitrones
cycloaddition
iminosugars
STEREOSELECTIVITY
pyrrolizidines
stereoselective synthesis
NATURAL OCCURRENCE
THREOSE DERIVED NITRONES
D-ERYTHROSE
ALKALOIDS
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Summary:A convenient and efficient method has been used for the synthesis of ten new tetrahydroxylated pyrrolizidines 12a, b, 13a-c, 14a, b, and 15a-c starting from sugar-derived cyclic nitrones prepared from D-xylose, D-arabinose, D-ribose, and L-arabinose, through a five-step reaction sequence. Pyrrolizidine 12a is an enantiomer of 7-deoxycasuarine and pyrrolizidine 12b an enantiomer of the as yet unknown 7-deoxyuniflorine A. This method expands the scope of nitrone cycloadditions and is flexible enough for the synthesis of various stereoisomers of highly polyhydroxylated pyrrolizidines.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1260933