131013-30-4

Upstream product

• 131013-28-0 (2S,3S,5S)-2-(phenylmethyl)-1-carbomethoxy-5-<(Z)-nonen-1-yl>-3-pyrrolidinol 
• 131013-29-1 (2S,3S,5S)-2-(phenylmethyl)-1-carbomethoxy-5-<(E)-nonen-1-yl>-3-pyrrolidinol 
• 351453-59-3 (2S,3S)-3-tert-butyldimethylsilyloxy-2-methoxycarbonylamino-1-phenyltetradecan-3-one 
• 127041-76-3 ((1S,2S)-1-Benzyl-2-hydroxy-pent-4-enyl)-carbamic acid benzyl ester 
• 337963-33-4 (2S,3S,5S)-2-Benzyl-3-hydroxy-5-hydroxymethyl-pyrrolidine-1-carboxylic acid methyl ester 
• 131013-23-5 methyl 6-C-phenyl-5-azido-3,5,6-trideoxy-2-O-<(trifluoromethyl)sulfonyl>-β-L-talofuranoside 
• 131013-24-6 methyl 6-C-phenyl-5-azido-3,5,6-trideoxy-2-O-<(trifluoromethyl)sulfonyl>-α-L-talofuranoside 
• 131013-22-4 methyl 6-C-phenyl-5-azido-3,5,6-trideoxy-α-L-talofuranoside 
• 131013-21-3 methyl 6-C-phenyl-5-azido-3,5,6-trideoxy-β-L-talofuranoside 
• 131100-32-8 methyl (3S,6S)-6-(phenylmethyl)-3-methoxy-2-oxa-5-azabicyclo<2.2.1>heptane-5-carboxylate 
• 131013-26-8 methyl (3R,6S)-6-(phenylmethyl)-3-methoxy-2-oxa-5-azabicyclo<2.2.1>heptane-5-carboxylate 
• 131013-25-7 (3R,6S)-6-(phenylmethyl)-3-methoxy-2-oxa-5-azabicyclo<2.2.1>heptane 
• 131100-31-7 (3S,6S)-6-(phenylmethyl)-3-methoxy-2-oxa-5-azabicyclo<2.2.1>heptane 
• 131013-18-8 6-C-phenyl-3,6-dideoxy-5-O-(p-tolylsulfonyl)-1,2-O-isopropylidene-α-D-allofuranose 

Downstream Products

• 125356-66-3 (+)-preussin 

Relevant academic research and scientific papers

Efficient stereoselective synthesis of (2s,3s,5r)-(+)-preussin

Allyltrimethylsilane reacted with N-carbobenzoxy-L-phenylalaninal to afford with high diastereoselectivity syn-adduct which was subsequently transformed into (2S, 3S, SR)-(+)-preussin.

A concise synthesis of (+)-preussin

A concise synthesis of (+)-preussin (1), an antifungal agent and a growth-inhibitor of fission yeast and human cancer cells, was accomplished employing a stereoselective aldol reaction between the zinc enolate of 2-undecanone and N-protected-L-phenylalaninal followed by reductive pyrrolidine formation as key steps.

The synthesis of (+)-preussin and related pyrrolidinols by diastereoselective Paterno-Buechi reactions of chiral 2-substituted 2,3-dihydropyrroles

The N-alkoxycarbonyl substituted 2,3-dihydropyrroles 3 and 8 are converted to 2-benzyl-3-pyrrolidinols by the Paterno - Buechi reaction followed by hydrogenolysis. Since the addition of the photoexcited benzaldehyde at the unsaturated heterocycle proceeds in a syn fashion, the benzyl group at C-2 and the hydroxy group at C-3 of the product are cis oriented. The simple and facial diastereoselectivities of the Paterno -Buechi reaction were studied more closely and the relative configuration of the products was elucidated. The thermodynamically less stable endo product is formed as a result of simple diastereo-selection. The face differentiation in 2-substituted 2,3-dihydropyrroles is presumably due to the nonplanarity of these heterocycles, which forces attack of the carbonyl group on the face with the existing substituent. All-cis-pyrrolidinols are consequently formed after hydrogenolysis. Following this route, a total synthesis of the pyrrolidinol alkaloid (+)-preussin (1) was conducted, which yielded the target compound in a total yield of 11% over nine steps starting from L-pyroglutaminol (11).