146554-64-5

Upstream product

• 18107-18-1 diazomethyl-trimethyl-silane 
• 197219-15-1 6-[(4-methoxyphenyl)methoxy]-2-hexyn-1-ol 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 102195-80-2 (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 1025953-11-0 2-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-4-[3-(4-methoxy-benzyloxy)-propyl]-hex-4-enoic acid methyl ester 
• 292046-35-6 (S)-2-tert-Butoxycarbonylamino-3-{(2R,3S)-3-hydroxymethyl-2-[3-(4-methoxy-benzyloxy)-propyl]-oxiranyl}-propionic acid methyl ester 
• 292046-34-5 (S)-2-tert-Butoxycarbonylamino-4-[2-hydroxy-eth-(Z)-ylidene]-7-(4-methoxy-benzyloxy)-heptanoic acid methyl ester 
• 292046-37-8 (S)-2-tert-Butoxycarbonylamino-3-[(S)-2-((S)-1,2-dihydroxy-ethyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester 
• 292046-36-7 (S)-2-tert-Butoxycarbonylamino-3-[(2R,3S)-3-hydroxymethyl-2-(3-hydroxy-propyl)-oxiranyl]-propionic acid methyl ester 
• 292046-29-8 (Z)-1-(tert-butyldimethylsiloxy)-3-iodo-6-(p-methoxybenzyl)oxy-2-hexene 
• 292046-38-9 (5S,8S)-6-Oxo-1-oxa-7-aza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-tert-butyl ester 8-methyl ester 
• 146554-63-4 methyl (8S)-7-tert-butoxycarbonyl-2-oxo-1-oxa-7-azaspiro<4.4>nonane-8-carboxylate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 

Downstream Products

• 69086-72-2 (+)-lycoperdic acid 

Relevant academic research and scientific papers

Diastereoselective synthesis of glutamate-appended oxolane rings: Synthesis of (S)-(+)-lycoperdic acid

(Chemical Equation Presented) The stereocontrolled synthesis of the glutamate-containing natural product (S)-(+)-lycoperdic acid is described. The key transformation in the synthetic route was an efficient diastereoselective annulation of an oxolane ring

Stereocontrolled synthesis of (+)-lycoperdic acid based on a palladium catalyzed reaction using a serine-derived organozinc reagent

An efficient stereocontrolled synthesis of (+)-lycoperdic acid has been achieved based on palladium catalyzed cross-coupling reaction of (Z)-1-(tert- butyldimethylsiloxy)-3-iodo-6-(p-methoxybenzyl)oxy-2-hexene with the organozinc reagent, prepared from N-Boc-β-iodoalanine methyl ester. (C) 2000 Elsevier Science Ltd.

Asymmetric synthesis of lycoperdic acid

Lycoperdic acid [(2S,5'S)-2-amino-3-(5'-carboxy-2'-oxo-5'- tetrahydrofuranyl)propanoic acid], isolated from the mushroom Lycoperdon perlatum, was synthesized from trans-4-hydroxy-L-proline by a six-step route involving samarium diiodide (SmI2)-mediated formation of the spiro-γ- lactone and ruthenium tetroxide (RuO4) oxidation of the L-proline ring system to the L-pyroglutamic acid moiety. Lycoperdic acid (1) was found to undergo hydrolysis of the γ-lactone ring in 1 N hydrochloric acid at 23°C, giving an equilibrated mixture of 1 and the corresponding hydroxy acid.

FIRST SYNTHESIS OF LYCOPERDIC ACID

Lycoperdic acid, (2S,2'S)-2-amino-3-(2'-carboxy-5'-oxo-2'-tetrahydrofuranyl)propanoic acid, was synthesized from trans-4-hydroxy-L-proline.