170423-76-4

Upstream product

• 164921-78-2 (E)-5-Acetoxy-4-(2-methoxy-4-methyl-phenyl)-pent-2-enoic acid methyl ester 
• 170423-73-1 (S)-1-[5-(benzyloxy)pentan-2-yl]-2-methoxy-4-methylbenzene 
• 170240-78-5 1-iodo-(4S)-(2-methoxy-4-methylphenyl)pentane 
• 170423-74-2 (4S)-(2-methoxy-4-methylphenyl)hexanenitrile 
• 170423-70-8 (S)-5-Hydroxy-4-(2-methoxy-4-methyl-phenyl)-pentanoic acid methyl ester 
• 170423-66-2 methyl (4S)-(2-methoxy-4-methylpenyl)-5-hydroxypentanoate 
• 170423-71-9 methyl (4S)-(2-methoxy-4-methylphenyl)-5-tosyloxypentanoate 
• 170423-68-4 (E)-(S)-5-Acetoxy-4-(2-methoxy-4-methyl-phenyl)-pent-2-enoic acid methyl ester 
• 164921-74-8 methyl 4-(2'-methoxy-4'-methylphenyl)-5-hydroxy-(2E)-pentanoate 
• 214629-65-9 2,2-Dimethyl-propionic acid (4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-5-(2-methoxy-4-methyl-phenyl)-hexyl ester 
• 214629-64-8 tert-Butyl-[(1S,2R)-2-(2-methoxy-4-methyl-phenyl)-cyclohex-3-enyloxy]-dimethyl-silane 
• 186581-53-3 diazomethane 
• 170423-75-3 methyl-(5S)-(2-methoxy-4-methylphenyl)hexanoate 
• 214629-66-0 2,2-Dimethyl-propionic acid (4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(2-methoxy-4-methyl-phenyl)-hexyl ester 

Downstream Products

• 109028-15-1 (S)-2-(6-hydroxy-6-methylheptan-2-yl)-5-methylphenol 

Relevant academic research and scientific papers

Total synthesis of (S)-(+)-curcudiol, and (S)-(+)- and (R)-(-)-curcuphenol1)

A highly enantioselective synthesis of the versatile chiral synthons possessing one stereogenic center, (S)-and (R)-4-aryl-5-hydroxy-(2E)-pentenoate (3) was achieved based on the enzymatic reaction of (±)-3 with commercially available lipases MY-30 or OF-360 from Candida rugosa. Application of (S)-3 and (R)-3 to the total syntheses of (S)-curcuphenol (1), (S)-curcudiol (2), and (R)-curcuphenol (1), respectively, is described.

Enantioselective construction and utilization of 2-(cyclohex-2-enyl)phenols

Enantioselective construction of 2-(cyclohex-2-enyl)phenols from chiral equivalents of cyclohex-2-enols has been investigated by employing a concurrent retro-Diels-Alder reaction and Claisen rearrangement protocol. Utilizing the enantiomerically pure product obtained, the first enantiocontrolled synthesis of a phenolic natural sesquiterpene (+)-curcudiol, isolated from the marine sponge Didiscus flavus, has been demonstrated.

Total Synthesis of (S)-(+)-Curcudiol, (S)- and (R)-(-)-Curcuphenol Based on Enzymatic Resolution of a Primary Alcohol Possessing One Stereogenic Center

A highly stereoselective synthesis of the versatile chiral synthons possessing one stereogenic center, (S)-3 and (R)-3 was achieved and the application of (S)-3 and (R)-3 into the total syntheses of (S)-curcuphenol (1), (S)-curcudiol (2), and (R)-curcuphenol (1), respectively, was described.