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Acid - catalyzed rearrangement of butyl 2-0-acetyl-4,5-anhydro-3,6-dideoxy-hexaldonate. Synthesis of racemic epiallomuscarine and epimuscarine

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
41
Issue
24
Identifiers
DOI: 10.1016/s0040-4020(01)91432-2

Abstract

Abstract Butyl 2-0-acetyl-4,5-anhydro-3,6-dideoxy-DL- xylo-hexaldonate ( 4 ) in the presence of SnCl 4 underwent an intramolecular rearrangement to give 2,5-anhydro ester 7 . On the other hand the lyxo epimeric epoxide 5 under the same conditions afforded esters 7 and 8 . Ester 7 was transformed into racemic epiallomuscarine ( 12 ), whereas the isomer 8 into racemic epimuscarine ( 13 ).

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