Asymmetric Synthesis of 2,4,6-Trideoxy-4-(dimethylamino)-3-C-methyl-Llyxohexopyranose (Lemonose)

L-Lemonose, the glycosidic part of (–)-lemonomycin, has been synthesized in ten steps with 18% overall yield from Dthreonine. The key steps are a double, highly diastereoselective Grignard addition to a Weinreb amide and a chemoselective oxidation of a primary alcohol in the presence of a secondary alcohol, a tertiary alcohol and a tertiary amine, leading directly to the lactol.


Published in:
Synlett, 4, 576-578
Year:
2011
Publisher:
Georg Thieme Verlag
ISSN:
0936-5214
Keywords:
Laboratories:




 Record created 2011-04-04, last modified 2018-03-17


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)