170235-99-1

Upstream product

• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 170235-98-0 4-(2,5-Bis-methoxymethoxy-4-methyl-phenyl)-pentanal 
• 4434-77-9 2-bromo-6-methylhept-5-ene 
• 681473-22-3 2,5-bis(methoxymethoxy)-4-bromotoluene 
• 4630-06-2 6-methylhept-5-en-2-ol 
• 62047-97-6 4-(2'-methoxy-4'-methylphenyl)pentanol 
• 87848-77-9 4-(o-methoxy-p-tolyl)-pentanoic acid methyl ester 
• 24599-58-4 2,5-dimethoxy toluene 
• 78508-74-4 methyl (2E)-3-<(2RS)-oxiran-2-yl>prop-2-enoate 
• 164921-92-0 methyl 4-(2',5'-dimethoxy-4'-methylphenyl)-5-hydroxy-(2E)-pentanoate 
• 170235-91-3 methyl 4-(2',5'-dimethoxy-4'-methylphenyl)-5-tosyloxypentanoate 
• 170235-96-8 4-(2',5'-dimethoxymethyloxy-4'-methylphenyl)pentyl acetate 
• 170235-97-9 4-(2',5'-dimethoxymethyloxy-4'-methylphenyl)pentanol 
• 170235-95-7 Acetic acid 4-(2,5-dihydroxy-4-methyl-phenyl)-pentyl ester 

Downstream Products

• 78964-28-0 (+/-)-curcuquinone 
• 78964-27-9 (+/-)-curcuhydroquinone 

Relevant academic research and scientific papers

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.

Reaction of methyl 4,5-epoxy-(2E)-pentenoate with arenes. II. Application to the synthesis of(±)-curcudiol, (±)-curcuphenol, (±)-curcuhydroquinone, and(±)-curcuquinone

Four bisabolane sesquiterpenes, (±)-curcudiol (2), (±)-curcuphenol (3), (±)-curcuhydroquinone (5) and (±)-curcuquinone (6), were synthesized based on the reaction of methyl 4,5-epoxy-(2E)-pentenoate (1) with methoxytoluenes in the presence of boron trifluoride etherate.

A FACILE SYNTHESIS OF 4-ARYL-5-HYDROXY-(2E)-PENTENOATE DERIVATIVES AND ITS APPLICATIONS TO THE FIRST SYNTHESIS OF (+/-)-CURUCUDIOL, (+/-)-CURCUHYDROQUINONE AND (+/-)-CURCUQUINONE

The first syntheses of three kinds of bisabolane sesquiterpenes, (+/-)-curcudiol (29), (+/-)-curcuhydroquinone (40) and (+/-)-curcuquinone (41) were achieved based on the BF3*Et2O catalyzed reaction of (+/-) methyl 4,5-epoxy-(2E)-pentenoate (1) and polyme