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A Facile and Rapid Route to a New Series of Pyrrolizidines Structurally Related to (+)‐Alexine and (+)‐Australine
Author(s) -
Behr JeanBernard,
Erard Audrey,
Guillerm Georges
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200204)2002:7<1256::aid-ejoc1256>3.0.co;2-r
Subject(s) - chemistry , dihydroxylation , intramolecular force , nucleophile , stereochemistry , chloride , series (stratigraphy) , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , biology , paleontology
Abstract Addition of allylmagnesium chloride to protected L ‐xylofuranosylamine gave, after intramolecular cyclization, the corresponding polyhydroxylated 2‐allylpyrrolidines. New series of analogues of (+)‐alexine and (+)‐australine were readily obtained from these intermediates by dihydroxylation, intramolecular nucleophilic displacement and subsequent deprotection. The determination of the configuration at the newly formed stereocentres was based on NMR experiments. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)