Synthesis of 1-Deoxy-d-galactohomonojirimycin via Enantiomerically Pure Allenylstannanes
- 12 December 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (7), 2229-2234
- https://doi.org/10.1021/jo0303012
Abstract
1-Deoxy-d-galactohomonojirimycin was synthesized in seven steps from optically pure allenylstannane 4 and l-lactate-derived aldehyde 5 in 48% overall yield. The key step was the Lewis acid catalyzed reaction of 4 and 5 to give the syn-amino alcohol in excellent yield and very high diastereoselectivity.Keywords
This publication has 35 references indexed in Scilit:
- Asymmetric synthesis of (+)-1-deoxynojirimycin and (+)-castanospermineTetrahedron, 2003
- Total synthesis of deoxymannojirimycin and d-mannolactam via carbonylation of 5-vinyloxazolidin-2-onesTetrahedron, 2003
- Synthetic access to 5,10-disubstituted porphyrinsTetrahedron Letters, 2003
- Recent Advances in the Synthesis of Naturally Occurring Polyhydroxylated AlkaloidsCurrent Organic Chemistry, 2002
- Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: asymmetric synthesis of 1-deoxynojirimycinTetrahedron Letters, 2001
- Radical Cyclization in Heterocycle Synthesis. Part 9: A Novel Synthesis of Aminocyclitols and Related Compounds via Stannyl Radical Cyclization of Oxime Ethers Derived from SugarsTetrahedron, 2000
- Synthesis of 1-Deoxynojirimycin and N-Butyl-1-deoxynojirimycinSynthesis, 1999
- Asymmetric synthesis of (+)-1-deoxynojirimycinTetrahedron Letters, 1998
- A Short Synthesis of Polyhydroxylated Piperidines by Aldol Reaction of Chelated Amino Acid Ester EnolatesEuropean Journal of Organic Chemistry, 1998
- Catalytic mechanism of enzymic glycosyl transferChemical Reviews, 1990