89015-46-3

Upstream product

• 88947-99-3 2-Hydroxy-2-methyl-6-(3-methoxy-4-methylphenyl)-heptane 
• 3556-81-8 1-(3-methoxy-4-methylphenyl)ethan-1-one 
• 37586-57-5 4-methyl-3-pentenylmagnesium bromide 
• 179754-27-9 Toluene-4-sulfonic acid 2-(3-methoxy-4-methyl-phenyl)-6-methyl-hept-5-enyl ester 
• 78508-74-4 methyl (2E)-3-<(2RS)-oxiran-2-yl>prop-2-enoate 
• 179754-23-5 (E)-4-(3-Methoxy-4-methyl-phenyl)-pent-2-ene-1,5-diol 
• 179754-24-6 (E)-5-Hydroxy-4-(3-methoxy-4-methyl-phenyl)-pent-2-enal 
• 179754-22-4 (E)-5-Hydroxy-2-(3-methoxy-4-methyl-phenyl)-pent-3-enoic acid methyl ester 
• 179754-26-8 2-(3-Methoxy-4-methyl-phenyl)-6-methyl-hept-5-en-1-ol 
• 179754-21-3 (E)-5-Hydroxy-4-(3-methoxy-4-methyl-phenyl)-pent-2-enoic acid methyl ester 
• 116425-58-2 ethyl 5-hydroxy-5-(3-methoxy-4-methylphenyl)-2-hexenoate 
• 116778-46-2 Ethyl 5-(3-methoxy-4-methylphenyl)hexanoate 
• 113706-59-5 2-(3-methoxy-4-methylphenyl)-6-methylhept-5-en-2-ol 
• 36138-76-8 5-bromo-2-methylphenol 

Downstream Products

• 59684-62-7 Xanthorrhizol 
• 113706-54-0 13-hydroxyxanthorrhizol 

Relevant academic research and scientific papers

Total Synthesis and Antibiotic Properties of Amino-Functionalized Aromatic Terpenoids Related to Erogorgiaene and the Pseudopterosins

Following a concept recently introduced by Hergenrother,[6] the present study addresses the question of whether certain antimicrobially active aromatic (marine) natural products can be converted into more potent broad-spectrum antibiotics by introducing an aminoalkyl side chain. To this end, phenolic mono- and sesquiterpenoids (incl. carvacrol, xanthorrhizol, and 7-hydroxycalamene) as well as the diterpenes 7-hydroxyerogorgiaene and 9-deoxypseudopterosin A were converted into amino-functionalized analogs that display either an amino-methyl or a 2-amino-ethoxy substituent in place of (or next to) the OH group. This was achieved either by Pd-catalyzed nitromethylation/reduction of the aryltriflates, by O-alkylation of the phenols with bromoacetonitrile and subsequent reduction, or by ortho-hydroxymethylation/amination. During the study, an efficient enantioselective total synthesis of 7-hydroxyerogorgiaene (8 steps, 29 % overall yield) and 9-deoxypseudopterosin A (9 steps, 30 % overall yield) was elaborated using an asymmetric cobalt-catalyzed hydrovinylation (91 % ee) of 3-methoxy-4-methyl-styrene as the chirogenic step. Other important C?C bond forming steps include a Pd-catalyzed Suzuki cross-coupling and diastereoselective Lewis acid-mediated cyclization reactions. A total of 16 amino derivatives of natural products were prepared and subsequently tested for their antibacterial properties. Some of the diterpene-derived amines showed high efficacy, not only against Gram-positive (S. aureus SG511, S. aureus HG003, B. subtilis 168; MIC=0.5 to 2 μg/ml), but also against Gram-negative bacterial strains (E. coli K12; E. coli I-11276b; MIC=8 to 32 μg/ml). This clearly supported the underlying working hypothesis.

Transition-Metal-Free Valorization of Biomass-derived Levulinic Acid Derivatives: Synthesis of Curcumene and Xanthorrhizol

Levulinic acid (LA) is acknowledged one of the most promising biomass-derived platform molecules and can be transformed into various value-added chemicals. Here, we report a new reaction process for the valorization of LA derivatives under transition-meta

A short synthesis of bisabolane sesquiterpenes

A facile total synthesis of three members of the bisabolane sesquiterpene family, namely (±)-curcumene, (±)-xanthorrhizol and (±)-curcuhydroquinone had been achieved in high overall yield. The synthesis used bromobenzene derivatives as starting materials.

Efficient total synthesis of racemic bisabolane sesquiterpenes curcuphenol and xanthorrhizol starting from substituted acetophenones

A total synthesis of natural bisabolane sesquiterpenes curcuphenol (1) and xanthorrhizol (2) was developed by using the substituted acetophenones 4 and 5, respectively, as starting materials. The acetyl group of the latter was activated through ethoxycarb

A formal total synthesis of xanthorrhizol based on nucleophilic opening of vinyloxirane by arylcopper reagent

A formal total synthesis of xanthorrhizol was achieved in short step sequence involving the nucleophilic opening of methyl 4,5-epoxy-(2E)-pentenoate (1) by arylcopper reagent.

A Short Synthesis of Xanthorrhizol

Reformatsky reaction of 3-methoxy-4-methylacetophenone (1) with ethyl 4-bromocrotonate (2) followed by hydrogenation over Pd-C in the presence of acetic acid gives ethyl 5-(3-methoxy-4-methylphenyl)hexanoate (4) in a high yield.Grignard reaction of 4 with

SYNTHESIS OF HYDROXYCADALENE AND HYDROXYCALAMENENE VIA 13-HYDROXYXANTHORRHIZOL, A POSSIBLE PRECURSOR OF PARVIFOLIN

Starting with an acetophenone derivative three sesquiterpenes, xanthorrhizol, hydroxycadalene and hydroxycalamenene were synthesized.The biomimetic formation of parvifolin could not be achieved.