154814-99-0

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 154815-14-2 (E)-(3R)-3-(benzyloxy)-4,6-heptadienol 
• 102794-92-3 (2R,4R)-4-formyl-2-phenyl-1,3-dioxane 

Downstream Products

• 154815-09-5 (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one 
• 154321-89-8 (4aS,5R)-5-(benzyloxy)-2,4a,5,6,7,8-hexahydropyrido<1,2-b><1,2>oxazin-8-one 
• 154815-10-8 (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-(isopropylidenedioxy)propyl>piperidin-6-one 
• 154815-08-4 (2R,3R)-3-(benzyloxy)-2-<(Z)-3-(tert-butyldiphenylsilyloxy)-1-propenyl>piperidin-6-one 
• 154815-06-2 (2S,3R)-3-(benzyloxy)-2-<(Z)-3-(tert-butyldimethylsilyloxy)-1-propenyl>piperidin-6-one 
• 154815-03-9 (3S,4R,4aR,5R)-5-(benzyloxy)-3,4-dihydroxy-2,3,4,4a,5,6,7,8-octahydropyrido<1,2-b><1,2>oxazin-9-one 
• 154815-11-9 (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-hydroxy-1,2-(isopropylidenedioxy)propyl>piperidine 
• 154815-12-0 (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine 
• 154815-05-1 (2S,3R)-3-(benzyloxy)-2-<(Z)-3-hydroxy-1-propenyl>piperidin-6-one 
• 154815-02-8 methyl (E)-(R)-4-(benzyloxy)-5,7-octadienoate 
• 154815-01-7 (E)-(R)-4-(benzyloxy)-5,7-octadienic acid 
• 154321-85-4 (E)-(R)-4-(benzyloxy)-N-hydroxy-5,7-octadienamide 
• 85624-09-5 (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol 
• 72741-87-8 swainsonine 

Relevant academic research and scientific papers

New Chiral Route to (-)-Swainsonine via an Aqueous Acylnitroso Cycloaddition Approach

A new noncarbohydrate-based enantioselective approach to (-)-swainsonine (1) is described, in which the aqueous intramolecular Diels-Alder reaction of a chiral acylnitroso diene has been employed as a key reaction.The intramolecular cycloaddition of the chiral hydroxamic acid 9, available from D-malic acid in 10 steps, with Pr4NIO4 was conducted under the conventional nonaqueous conditions using CHCl3 as a solvent, whereupon intermediacy acylnitroso compound 10 cyclized spontaneously to give the trans- and cis-1,2-oxazinolactams 11 and 12 with a low diastereoselection af 1.3:1 in 76percent combined yield.When the corresponding reaction was performed in water, it led to significant enhancements of trans selectivity of 4.1:1 as well as combined yield (89percent).The trans adduct 11 was subjected to reductive N-O bond cleavage followed by diastereoselective hydroxylation with OsO4 to provide the 1,2-glycol 21, which was then converted to the amino alcohol 25.Intramolecular cyclodehydration of 25 with CBr4/PPh3/Et3N and subsequent deprotection furnished (-)-swainsonine (1).