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1,3-Oxazine as a chiral building block used in the total synthesis of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)-dihydroxypyrrolidine
- Authors
- Park, SH[Park, Seok-Hwi]; Kim, JY[Kim, Ji-Yeon]; Kim, JS[Kim, Jin-Seok]; Jung, C[Jung, Changyoung]; Song, DK[Song, Dong-Keun]; Ham, WH[Ham, Won-Hun]
- Issue Date
- 15-Jul-2015
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Citation
- TETRAHEDRON-ASYMMETRY, v.26, no.12-13, pp.657 - 661
- Indexed
- SCIE
SCOPUS
- Journal Title
- TETRAHEDRON-ASYMMETRY
- Volume
- 26
- Number
- 12-13
- Start Page
- 657
- End Page
- 661
- ISSN
- 0957-4166
- Abstract
- Concise and stereocontrolled syntheses of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)dihydroxypyrrolidine [(+)-DMDP] were achieved via a diastereomerically enriched oxazine intermediate. The key strategies include the use of 1,3-oxazine as a chiral building block and diastereoselective nucleophilic addition to an aldehyde. Starting from readily available (R)-methyl 2-benzamido-3-((tertbutyldimethylsilyl)oxy)propanoate, (+)-1-deoxynojirimycin was synthesized in 11 steps and 26.2% overall yield while (+)-DMDP was synthesized in 11 steps and 27.1% overall yield, respectively. (C) 2015 Elsevier Ltd. All rights reserved.
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Collections - Pharmacy > Department of Pharmacy > 1. Journal Articles
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