162470-36-2

Upstream product

• 162470-35-1 (2S,3R,7S,8R)-3-benzyloxy-1-tosyl-2-(1',2',3'-trihydroxypropyl)piperidine 
• 1550202-88-4 tert-butyl (2S,3R)-3-(benzyloxy)-2-((1S,2R)-1,2,3-trihydroxypropyl)piperidine-1-carboxylate 
• 1550202-43-1 tert-butyl (2S,3R)-3-(benzyloxy)-2-((R)-1-hydroxyallyl)piperidine-1-carboxylate 
• 849928-65-0 (2R,3R)-3-Benzyloxy-2-formyl-piperidine-1-carboxylic acid tert-butyl ester 
• 1175524-38-5 (5R,6S)-tert-butyl 5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate 
• 849928-64-9 tert-butyl (2S,3R)-3-(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate 
• 1301261-35-7 tert-butyl (2S,3R)-3-(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)piperidine-1-carboxylate 
• 171366-60-2 N-<1-(2-furyl)-4-methoxymethoxybut-2-ynyl>toluene-p-sulfonamide 
• 162470-34-0 (2S,3R,7S,8R)-3-benzyloxy-2-(1',2'-dihydroxy-3'-methoxymethoxypropyl)-1-tosylpiperidine 
• 162470-28-2 N-<1-(2-furyl)-4-methoxymethoxybut-2-enyl>toluene-p-sulfonamide 
• 162470-32-8 (2S,3R,6S)-3-benzyloxy-6-ethoxy-2-<(Z)-3'-methoxymethoxyprop-1'-enyl>-1-tosylpiperidine 
• 162470-33-9 (2S,3R)-3-benzyloxy-2-<(Z)-3'-methoxymethoxyprop-1'-enyl>-1-tosylpiperidine 
• 162470-31-7 (2S,3R,6S)-6-ethoxy-2-<(Z)-3'-methoxymethoxyprop-1'-enyl>-1-tosylpiperidin-3-ol 
• 162470-30-6 (2S,6S)-6-ethoxy-2-<(Z)-3'-methoxymethoxyprop-1'-enyl>-1-tosyl-1,2,3,6-tetrahydropyridin-3-one 

Downstream Products

• 85624-09-5 (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol 
• 72741-87-8 swainsonine 
• 154815-12-0 (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine 

Relevant academic research and scientific papers

Synthesis of polyhydroxylated indolizidines and piperidines from Garner's aldehyde: Total synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, (+)-8,8a-di-epi-castanospermine, pentahydroxy indolizidines, (-)-1-deoxynojirimycin, (-)-1-deoxy-altro-nojirimycin, and related diversity

Diastereoselective and diverse synthesis of polyhydroxylated indolizidines and piperidines have been described, where a common chiral intermediate 2-(hydroxymethyl) piperidine-3-ol is converted into (-)-swainsonine, (+)-1,2-di-epi-swainsonine, (+)-8,8a-di-epi-castanospermine, pentahydroxy indolizidines, (-)-1-deoxynojirimycin, (-)-1-deoxy-altro-nojirimycin, and related diversity. The key steps were hydroxy directed intramolecular aminomercuration, Mitsunobu cyclization, and diastereoselective dihydroxylation.

Asymmetric synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, and (+)-1,2,8-tri-epi-swainsonine

The asymmetric synthesis of (-)-swainsonine via a nonchiral pool route that involves the Sharpless epoxidation to induce chirality is reported. The key steps involve vinyl epoxide aminolysis, ring-closing metathesis, and intramolecular N-alkylation to prepare the indolizidine ring and a highly diastereoselective cis-dihydroxylation using AD-mix-α. This synthetic strategy also allowed for the diastereoselective synthesis of (+)-1,2-di-epi-swainsonine and (+)-1,2,8-tri-epi-swainsonine.

Asymmetric formal total synthesis of (-)-swainsonine

A new concise noncarbohydrate-based enantioselective approach to (-)-swainsonine 1 is described, utilizing the kinetic resolution of α-furfuryl amide 4 and the Sharpless AD reaction of 9a as key steps.Kinetic resolution of α-furfuryl amide 4 using the mod

A New Approach to Indolizidine Alkaloids: Asymmetric Formal Total Synthesis of (-)-Swainsonine

A concise, noncarbohydrate-based approach to (-)-Swainsonine (1) has been achieved by utilizing the kinetic resolution of the α-furfuryl amide 4 and the Sharpless ADH reaction as key steps.