393563-18-3

Upstream product

• 393563-17-2 (4S)-N-[2-(3-indolyl)ethyl]-4-ethyl-4-(2-tert-butyldiphenylsiloxyethyl)-5-oxopentamide 
• 262847-04-1 (5S)-N-[2-(3-indolyl)ethyl]-5-ethyl-5-(2-tert-butyldiphenylsiloxyethyl)-6-hydroxy-δ-lactam 
• 121074-25-7 (4R,5S)-3-[(2S)-1-oxo-2-ethyl-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone 
• 393563-16-1 (4S)-N-[2-(indol-3-yl)-ethyl]-4-ethyl-4-hydroxymethyl-6-hydroxyhexamide 
• 262846-97-9 (2S)-[5-(tert-butyldiphenylsilyloxy)-2-ethylpentyl]-α-diazo-α-(methoxycarbonyl)acetate 
• 393563-08-1 (4R,5S)-3[(2R)-2-((1R*)-1-hydroxyethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone 
• 393563-09-2 (4R,5S)-3-[(2R)-2((1R*)-1-(phenoxythiocarbonyloxy)ethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone 
• 393563-10-5 (S)-2-ethylpent-4-enoic acid 
• 96930-18-6 (4R,5S)-4-methyl-3-pent-4-enoyl-5-phenyloxazolidin-2-one 
• 121074-21-3 (2S)-2-ethyl-4-penten-1-ol 
• 393563-15-0 (4S)-4-ethyl-4-(3-hydroxypropyl)dihydro-2(3H)-furanone 
• 262846-96-8 (4S)-4-ethyl-4-[2-(hydroxycarbonyl)ethyl]dihydro-2(3H)-furanone 
• 393563-11-6 methyl (S)-(2-ethyl-4-pentenyl)malonate 
• 393563-12-7 (2S)-(2-ethyl-5-hydroxypentyl)-α-(methoxycarbonyl)acetate 

Downstream Products

• 4880-88-0 vinburnine 

Relevant academic research and scientific papers

Total synthesis of (-)-eburnamonine and (+)-epi-eburnamonine from a chiral non-racemic 4,4-disubstituted γ-lactone

The total synthesis of (-)-eburnamonine and (+)-epi-eburnamonine was successfully achieved using a key chiral non-racemic 4,4-disubstituted γ- lactone 4 that was prepared via the Rh(II) carbenoid mediated tertiary C-H insertion reaction of a chiral non-racemic diazomalonate 5. (C) 2000 Elsevier Science Ltd.

Asymmetric synthesis of (-)-eburnamonine and (+)-epi-eburnamonine from (4s)-4-ethyl-4-[2-(hydroxycarbonyl)ethyl]-2-butyrolactone

The key chiral nonracemic 4,4-disubstituted 2-butyrolactone carboxylic acid, (S)-4, is readily accessible via an efficient and stereospecific dirhodium(II) tetraacetate catalyzed tertiary C-H insertion reaction of the diazomalonate (S)-5. The coupling of the acid (S)-4 with tryptamine produces the amide (S)-3, which is then transformed into the aldehyde 23 and hydroxy-lactam 24. Acid-mediated Pictet-Spengler cyclization of 23 and 24 produces the tetracyclic indole lactams (1S,-12bS)-25a and (1S,12bR)-25b. Compounds 25a and 25b are converted, via the lactam alcohols 30a and 30b, to (-)-eburnamonine (1a) and (+)-epi-eburnamonine (1b).