111833-07-9

Upstream product

• 110-93-0 6-Methyl-hept-5-en-2-on 
• 4535-64-2 5-methyl-1-phenylhex-4-en-1-one 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 180303-11-1 Trifluoro-methanesulfonic acid 5-methyl-1-methylene-hex-4-enyl ester 
• 23665-09-0 phenylzinc iodide 
• 17920-93-3 1-phenyl-6-methyl-5-hepten-2-ol 
• 870-63-3 prenyl bromide 
• 4535-59-5 ethyl 2-benzoyl-5-methylhex-4-enoate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Downstream Products

• 1026528-24-4 C₂₀H₃₄O₂Si 

Relevant academic research and scientific papers

Cyclization-endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst

Triarylpyrylium salts were employed as single electron photooxidants to catalyze a cyclization-endoperoxidation cascade of dienes. The transformation is presumed to proceed via the intermediacy of diene cation radicals. The nature of the diene component was investigated in this context to determine the structural requirements necessary for successful reactivity. Several unique endoperoxide structures were synthesized in yields up to 79%.

Synthesis of cyclic peroxides by chemo- and regioselective peroxidation of dienes with Co(II)/O2/Et3SiH

(Chemical Equation Presented). In the competitive peroxidation of mixtures of two alkenes with Co(II)/O2/Et3SiH, it was found that the relative reactivities of the alkene substrates are influenced by three major factors:. (1) relative stability of the intermediate carbon-centered radical formed by the reaction of the alkene with HCo(III) complex, (2) steric effects around the C=C double bond, and (3) electronic factors associated with the C=C double bond. Consistent with results from simple alkenes, the chemo-and regioselective peroxidation of dienes was also realized. Depending on the diene structure, the product included not only the expected acyclic unsaturated triethylsilyl peroxides but also 1,2-dioxolane and 1,2-dioxane derivatives via intramolecular cyclization of the unsaturated peroxy radical intermediates.

Synthesis of Aromatic Bisabolene Natural Products via Palladium-Catalyzed Cross-Couplings of Organozine Reagents

Aromatic bisabolene derivatives were prepared by two methods involving cross-coupling of organozinc reagents. The first synthesis of (±)-glandulone A (10), as well as syntheses of (± )-curcuhydroquinone (8) and (±)-curcuquinone (9), were accomplished via coupling of a secondary alkyl zinc reagent (1,5-dimethyl-4-hexenylzinc halide, 18) to protected bromohydroquinones using Pd(dppf)Cl2 as catalyst. Coupling of arylzinc halides with alkenyl triflate 16 using Pd(PPh 3)4 catalyst provided a number of bisabolene derivatives and led to syntheses of dehydro-α-curcumene (2), (±)-curcuphenol (3), and (±)-elvirol (13). A high-yield synthesis of the (±)-heliannuol D precursor 29 is also reported using this method.