98498-56-7

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 27763-54-8 (S)-2-methylbutanoyl chloride 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 1730-91-2 (S)-2-Methylbutyric acid 

Downstream Products

• 1333469-53-6 (S)-1-(2,4-bis((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)-2-methylbutan-1-one 
• 1131366-95-4 (2S)-1-(2-(((2E)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-4,6-dihydroxy-phenyl)-2-methylbutan-1-one 
• 5022-20-8 mammea B/BB 

Relevant academic research and scientific papers

Antibacterial acylphloroglucinols from hypericum olympicum

New antibacterial acylphloroglucinols (1-5) were isolated and characterized from the aerial parts of the plant Hypericum olympicum L. cf. uniflorum. The structures of these compounds were confirmed by extensive 1D- and 2D-NMR experiments to be 4,6-dihydroxy-2-O-(3″,7″-dimethyl-2″, 6″-octadienyl)-1-(2′-methylbutanoyl)benzene (1), 4,6-dihydroxy-2-O-(7″-hydroxy-3″,7″-dimethyl-2″, 5″-octadienyl)-1-(2′-methylbutanoyl)benzene (2), 4,6-dihydroxy-2-O-(6″-hydroxy-3″,7″-dimethyl-2″, 7″-octadienyl)-1-(2′-methylbutanoyl)benzene (3), 4,6-dihydroxy-2-O-(6″-hydroperoxy-3″,7″-dimethyl-2″, 7″-octadienyl)-1-(2′-methylbutanoyl)benzene (4), and 4,6-dihydroxy-2-O-(6″,7″-epoxy-3″,7″-dimethyloct- 2″-enyl)-1-(2′-methylbutanoyl)benzene (5). These new natural products have been given the trivial names olympicins A-E (1-5). All compounds were evaluated against a panel of methicillin-resistant Staph. aureus and multidrug-resistant strains of Staph. aureus. Compound 1 exhibited minimum inhibitory concentrations (MICs) of 0.5-1 mg/L against the tested Staph. aureus strains. Compounds 2 to 5 were also shown to be active, with MICs ranging from 64 to 128 mg/L. Compound 1 was synthesized using a simple four-step method that can be readily utilized to give a number of structural analogues of 1.

Total synthesis of acylphloroglucinols and their antibacterial activities against clinical isolates of multi-drug resistant (MDR) and methicillin-resistant strains of Staphylococcus aureus

Bioassay-directed drug discovery efforts focusing on various species of the genus Hypericum led to the discovery of a number of new acylphloroglucinols including (S,E)-1-(2-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-4,6-dihydroxyphenyl)-2-methylbutan-1-one (6, olympicin A) from H. olympicum, with MICs ranging from 0.5 to 1 mg/L against a series of clinical isolates of multi-drug-resistant (MDR) and methicillin-resistant Staphylococcus aureus (MRSA) strains. The promising activity and interesting chemistry of olympicin A prompted us to carry out the total synthesis of 6 and a series of analogues in order to assess their structure-activity profile as a new group of antibacterial agents. Following the synthesis of 6 and structurally-related acylphloroglucinols 7–15 and 18–24, their antibacterial activities against a panel of S. aureus strains were evaluated. The presence of an alkyloxy group consisting of 8–10 carbon atoms ortho to a five-carbon acyl substituent on the phloroglucinol core are important structural features for promising anti-staphylococcal activity.

Tricyclic Acylphloroglucinols from Hypericum lanceolatum and Regioselective Synthesis of Selancins A and B

The chemical investigation of the chloroform extract of Hypericum lanceolatum guided by 1H NMR, ESIMS, and TLC profiles led to the isolation of 11 new tricyclic acylphloroglucinol derivatives, named selancins A-I (1-9) and hyperselancins A and

Biomimetic Total Synthesis of Hyperjapones A–E and Hyperjaponols A and C

Hyperjapones A–E and hyperjaponols A–C are complex natural products of mixed aromatic polyketide and terpene biosynthetic origin that have recently been isolated from Hypericum japonicum. We have synthesized hyperjapones A–E using a biomimetic, oxidative

Synthesis, structure-activity relationship studies, and antibacterial evaluation of 4-chromanones and chalcones, as well as olympicin A and derivatives

On the basis of recently reported abyssinone II and olympicin A, a series of chemically modified flavonoid phytochemicals were synthesized and evaluated against Mycobacterium tuberculosis and a panel of Gram-positive and -negative bacterial pathogens. Some of the synthesized compounds exhibited good antibacterial activities against Gram-positive pathogens including methicillin resistant Staphylococcus aureus with minimum inhibitory concentration as low as 0.39 μg/mL. SAR analysis revealed that the 2-hydrophobic substituent and the 4-hydrogen bond donor/acceptor of the 4-chromanone scaffold together with the hydroxy groups at 5- and 7-positions enhanced antibacterial activities; the 2′,4′-dihydroxylated A ring and the lipophilic substituted B ring of chalcone derivatives were pharmacophoric elements for antibacterial activities. Mode of action studies performed on selected compounds revealed that they dissipated the bacterial membrane potential, resulting in the inhibition of macromolecular biosynthesis; further studies showed that selected compounds inhibited DNA topoisomerase IV, suggesting complex mechanisms of actions for compounds in this series.

Anti-Bacterial Agents

The invention relates to novel acylphloroglucinols which have strong growth inhibitory effects on multi-drug resistant strains of bacteria, particularly MRSA. Typically the compounds have a terpene substituent, or a terpene-derived substituent. Methods of

Synthesis of the Mammea Coumarins. Part 4. Stereochemical and Regiochemical Studies, and Synthesis of (-)-Mammea B/BB

Acylation of phloroglucinol with (S)-2-methylbutyryl chloride followed by Pechmann condensation with ethyl 3-oxohexanoate, or acylation of 5,7-dihydroxy-4-propylcoumarin with (S)-2-methylbutyryl chloride gave an 8-(S)-acylcoumarin that was C-alkylated to afford natural (-)-mammea B/BB: the configuration of the 2-methylbutyryl moiety in the natural coumarins was thus demonstrated to be (S)-Surangin B was likewise prepared as a mixture of 1'S, 2''S)- and (1'R, 2''S)-stereoisomers.The crystal structure and conformation of a 6-acylcoumarin that establishes the orientation of other synthetic coumarins is reported.