182412-80-2

Upstream product

• 50-00-0 formaldehyd 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 26732-90-1 3-(3-methyl-but-2-enyl)-pentane-2,4-dione 
• 75-16-1 methylmagnesium bromide 
• 215780-38-4 N-Methyl-N-methoxy-2-methylene-5-methylhex-4-enamide 
• 870-63-3 prenyl bromide 
• 123-54-6 acetylacetone 
• 54109-51-2 ethyl 5-methyl-2-methylenehex-4-enoate 
• 215780-36-2 2-Methylene-5-methylhex-4-enoic acid 

Downstream Products

• 215780-24-8 6-Methyl-3-{[((Z)-2-methyl-but-2-enyl)-diphenyl-silanyl]-methyl}-hept-5-en-2-one 
• 2051-33-4 2-isopropyl-5-methylhexan-1-ol 
• 1492897-02-5 C₁₆H₂₂OS 
• 942305-08-0 7-epi-clusianone 

Relevant academic research and scientific papers

Polycyclic Polyprenylated Acylphloroglucinols: An Emerging Class of Non-Peptide-Based MRSA- and VRE-Active Antibiotics

In the past 20 years, peptide-based antibiotics, such as vancomycin, teicoplanin, and daptomycin, have often been considered as second-line antibiotics. However, in recent years, an increasing number of reports on vancomycin resistance in pathogens appear

The enantioselective total synthesis of (+)-clusianone

(+)-Clusianone, an exo-type B PPAP with reported anti-HIV and chemoprotective activities, was synthesized in eleven steps with 97% ee starting from acetylacetone. An enantioselective decarboxylative Tsuji-Trost-allylation and a Ru-catalyzed ring-closing metathesis-decarboxylative allylation were used to control both diastereo- and enantioselectivity.

The total synthesis of hyperpapuanone, hyperibone L, epi-clusianone and oblongifolin A

Polyprenylated polycyclic acylphloroglucines (PPAPs) are a family of natural products that possess a wide range of different important biological activities because of the relative position and configuration of four substituents that decorate one common c

Sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives

In search for new methods aiming biomimetic synthesis of polyprenylated acylphloroglucinols (PPAPs), we now report the results of an evaluation of sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives, in neutral conditions. As a result, conditions were found for rather efficient C-prenylation of these compounds. The corresponding trimethyl ether gave the best results, but the reaction was accompanied by a deacylation process. Geranyl transfer was also observed, but in low yield, and, interestingly, an isolavandulyl group could be introduced with an appreciable yield.

A synthesis of (±)-lavandulol using a silyl-to-hydroxy conversion in the presence of 1,1-disubstituted and trisubstituted double bonds

Silylcuprates and silylzincates react with α,β-unsaturated aldehydes, esters, ketones and amides 19 unsubstituted at the β-position in higher yield if trimethylsilyl chloride is present. Applying this method, conjugate addition of the silylcuprate 26 derived from (Z)-chloro(2-methylbut-2-enyl)diphenylsilane 24, itself prepared by an improved route, to 3-methylene-6-methylhept-5-en-2-one 25 gave 3-[(Z)-2-methylbut-2-enyl(diphenyl)silyl]methyl-6-methylhept-5-en-2-one 27. A Wittig reaction gave 3-[(Z)-2-methylbut-2-enyl(diphenyl)silyl]methyl-2,6-dimethylhepta-1,5-diene 28 and silyl-to-hydroxy conversion gave lavandulol 1, even in the presence of the 1,1-disubstituted and trisubstituted double bonds. The hydroxy group of the 3-hydroxysilane, 2,6-dimethyl-3-{[(Z)-2-methylbut-2-enyl]diphenylsilyl}methylhept-5-en-2-ol 30, activated the allylsilane group towards protodesilylation. Chloro(diphenyl)methallylsilane 35 is easier to make than the chloride 24, and should be an alternative allylsilane that can make a lithium and hence a cuprate reagent like 26.