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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 7
BKCSDE 30(7)
July 20, 2009 

 
Title
Stereoselective Synthesis of L-Deoxyaltronojirimycin from L-Serine
Author
Rajesh Rengasamy, Marcus J Curtis Long, Hyung Won Ryu, Kyeong Yeol Oh, Ki Hun Park*
Keywords
Polyhydroxylated piperidine, Azasugars, L-Deoxyaltronojirimycin, Vinyl magnesium bromide, Ring closing metathesis
Abstract
(2S,3R)-3-Hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine 8, an important precursor for the synthesis of polyhydroxylated piperidine azasugars, has been prepared from L-serine. Highly stereoselective nucleophilic addition to amino aldehyde 5 gave the corresponding allylic alcohol 6 which proceeded to give dihydro-2H-piridine 7a via a Grubbs II catalyzed RCM. Stereoselective H-bond directed epoxidation of allylic alcohol led to the oxiranyl alcohol 9 which was easily converted to L-deoxyaltronojirimycin by regioselective ring opening.
Page
1531 - 1534
Full Text
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