Current time in Korea 11:01 Jul 31 (Sat) Year 2021 KCS KCS Publications
KCS Publications
My Journal  Log In  Register
HOME > Search > Browsing(BKCS) > Archives

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 

Stereoselective Synthesis of L-Deoxyaltronojirimycin from L-Serine
Rajesh Rengasamy, Marcus J Curtis Long, Hyung Won Ryu, Kyeong Yeol Oh, Ki Hun Park*
Polyhydroxylated piperidine, Azasugars, L-Deoxyaltronojirimycin, Vinyl magnesium bromide, Ring closing metathesis
(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.
1531 - 1534
Full Text
PDF / Supporting Information