The first enantioselective synthesis of imino-deoxydigitoxose and protected imino-digitoxose by using l-threonine aldolase-catalyzed aldol condensation

The first enantioselective synthesis of imino-deoxydigitoxose and protected imino-digitoxose by using l-threonine aldolase-catalyzed aldol condensation

The first enantioselective synthesis of protected imino-digitoxose (−)- 16 was attained starting with a synthetic intermediate of polyoxin C prepared by the l-threonine aldolase-catalyzed aldol condensation of (2 S,3 S)-2,3- O-isopropyriden-4-penten-1-al 8 and glycine. The strategy took advantage of...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron: asymmetry Vol. 20; no. 2; pp. 230 - 234
Main Authors: Nishiyama, Toshihiro, Kajimoto, Tetsuya, Mohile, Swapnil S., Hayama, Noboru, Otsuda, Teppei, Ozeki, Minoru, Node, Manabu
Format: Journal Article
Language:English
Published: Elsevier Ltd 12-02-2009
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The first enantioselective synthesis of protected imino-digitoxose (−)- 16 was attained starting with a synthetic intermediate of polyoxin C prepared by the l-threonine aldolase-catalyzed aldol condensation of (2 S,3 S)-2,3- O-isopropyriden-4-penten-1-al 8 and glycine. The strategy took advantage of an intramolecular nucleophilic attack by a Cbz-protected amino group on the hemiacetal carbon, a side reaction in the synthesis of natural products, for the formation of the piperidine ring of the imino-sugar. Imino-deoxydigitoxose (+)- 18 was also synthesized from (−)- 16 by reduction and acid hydrolysis.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2008.12.029