69086-72-2

Basic information

• Product Name: (+)-Lycoperdic acid
• Synonyms: (+)-Lycoperdic acid;(2S)-2-Amino-3-[(2S)-2-carboxy-5-oxotetrahydrofuran-2-yl]propionic acid;(2S,αS)-Tetrahydro-α-amino-2-carboxy-5-oxo-2-furanpropionic acid;Lycoperdic acid
• CAS NO: 69086-72-2
• Molecular Formula: C8H11NO6
• Molecular Weight: 217.17604
• Mol File: 69086-72-2.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-Lycoperdic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Lycoperdic acid(69086-72-2)
• EPA Substance Registry System: (+)-Lycoperdic acid(69086-72-2)

Safety Data

• Hazardous Substances Data: 69086-72-2(Hazardous Substances Data)

Usage

Uses

Lycoperdic Acid comes from the fungi Lycoperdon perlatum. This compound helps give the fruiting body its pungent odor as well as exhibits anti microbial properties.

Upstream product

• 324535-77-5 ((3aR,4S,6R,6aS)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester 
• 3008-40-0 cyclopentane-1,2-dione 
• 3019-83-8 3-bromo-2-hydroxycyclopent-2-en-1-one 
• 51-35-4 4R-4-hydroxyproline 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 

Relevant articles and documents

Total synthesis of lycoperdic acid and its C4-epimer

Efficient stereodivergent syntheses of (+)-lycoperdic acid (LPA) and 4-epi-LPA have been achieved based on asymmetric hydrogenation (H2, Rh/(R,S)-MeBoPhoz) of racemic enamide as a key step.

3-Alkyl-1,2-cyclopentanediones by Negishi cross-coupling of a 3-bromo-1,2-cyclopentanedione silyl enol ether with alkylzinc reagents: An approach to 2-substituted carboxylic acid γ-lactones, homocitric and lycoperdic acids

Negishi cross-coupling of the silyl-protected 3-bromoenol of 1,2-cyclopentanedione with primary and secondary alkylzinc reagents using Pd-catalysts affords 3-alkyl substituted 1,2-cyclopentanediones in good yield. The method was applied to obtain 3-methyl

Stereoselective syntheses of 4-hydroxy 4-substituted glutamic acids

The 4-hydroxy 4-substituted glutamic acid moiety is a common substructure of biologically important natural products such as monatin [(2S,4S)-2], lycoperdic acid (3), and dysiherbaine (4). To develop methodology for syntheses of these natural products, cycloadditions of nitrone 5 with 2-substituted 2-propen-1-ols 6 and 2-substituted acrylates 8 were investigated. Reactions of nitrone 5 with alcohols 6 in the presence of MgBr2OEt2 gave cycloadducts 7 in a highly stereoselective manner, whereas noncatalyzed reactions of 5 with acrylates 8 afforded adducts 9. Using the former reaction, syntheses of monatin [(2S,4S)-2], monatin derivative 18, and lycoperdic acid (3) were accomplished. The C4-epimer of monatin [(2S,4R)-2)] was also synthesized by employing the latter cycloaddition.