153277-28-2

Upstream product

• 153277-27-1 (2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 130948-04-8 Methyl 1-(tert-butoxycarbonyl)-3-oxopyrrolidine-2-carboxylate 
• 118449-01-7 (2R,3S)-3-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 170123-25-8 3-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 146256-97-5 3-(tert-butoxycarbonyl-ethoxycarbonylmethyl-amino)-propionic acid ethyl ester 
• 153277-24-8 (2S,3S)-1-(tert-Butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine-2-methanol 
• 153277-25-9 (2R,3S)-1-(tert-Butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine-2-carbaldehyde 
• 194924-97-5 Methyl (2R,3S)-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine-2-carboxylate 
• 153277-33-9 N-benzyloxycarbonyl-S-phenyl-L-cysteine methyl ester 
• 132249-34-4 Methyl (S)-2-benzyloxycarbonylamino-3-methylsulfonyloxypropanoate 
• 153277-34-0 (R)-2-Benzyloxycarbonylamino-1-(tert-butyldimethylsilyloxy)-3-phenylthiopropane 
• 153277-21-5 (R)-2-Benzyloxycarbonylamino-1-(tert-butyldimethylsilyloxy)-3-phenylsulfonylpropane 
• 153277-26-0 (2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine 

Downstream Products

• 153277-31-7 (2S,3S)-2-((S)-3-Benzyloxycarbonylamino-4-hydroxy-butyl)-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 20084-93-9 (1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizidine 
• 153379-64-7 O-Deacetyl-N-(benzyloxycarbonyl)slaframine 
• 153277-29-3 ((1S,6S,8aS)-1-Methoxymethoxy-octahydro-indolizin-6-yl)-carbamic acid benzyl ester 
• 153379-66-9 (1S,6S,8aS)-6-(benzyloxycarbonylamino)octahydroindolizin-1-yl acetate 
• 153277-32-8 (2S,3S)-2-((S)-3-Benzyloxycarbonylamino-4-methanesulfonyloxy-butyl)-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 20084-93-9 (-)-slaframine 

Relevant academic research and scientific papers

Total synthesis of (-)-slaframine from (2R,3S)-3-hydroxyproline

The yeast reduction products (2R,3S)-N-Boc-3-hydroxyproline esters 23 have been converted into the 3-methoxymethoxyprolinal 26 which undergoes an efficient Julia olefination with the L-serine-derived amino sulfone 29. Selective reduction of the resulting alkene 31 using diimide and cyclization leads to N-(benzyloxycarbonyl)slaframine 33c and thence to natural (-)-slaframine 5 and its more stable, crystalline N-acetyl derivative 34.

A total synthesis of (-)-slaframine from (+)-cis-(2R,3S)-3-hydroxyproline

A total synthesis of the naturally occurring indolizidine (-)-Slaframine 4 has been achieved, starting from the cis-3-hydroxyproline derivative 1, in which a key step is a Julia olefination reaction using the dianion derived from the β-aminosulfone 5.