960367-63-9

Upstream product

• 898538-91-5 3-[2-(2-hydroxy-1,1-dimethylethoxy)-5-methoxy-4-methylphenyl]-prop-2-en-1-ol 
• 78-39-7 Triethyl orthoacetate 
• 55939-26-9 6-methoxy-7-methylcoumarin 
• 898538-86-8 3-[2-(1-carboxy-1-methyl-ethoxy)-5-methoxy-4-methyl-phenyl]-acrylic acid 
• 75786-73-1 6-hydroxy-7-methyl-2H-chromen-2-one 

Downstream Products

• 898538-92-6 ethyl 3-[2-(2-hydroxy-1,1-dimethylethoxy)-5-methoxy-4-methylphenyl]-4-pentenoate 
• 898538-85-7 ethyl 3-[5-methoxy-2-(1-methoxycarbonyl-1-methyl-ethoxy)-4-methylphenyl]-4-pentenoate 
• 898538-94-8 3-[2-(1-carboxy-1-methyl-ethoxy)-5-methoxy-4-methyl-phenyl]-pent-4-enoic acid ethyl ester 

Relevant academic research and scientific papers

Bargellini condensation of coumarins. Expeditious route to o-carboxyvinylphenoxyisobutyric acids and application to the synthesis of sesquiterpenes helianane, heliannuol A and heliannuol C

The direct Bargellini condensation of coumarins involving reaction with chloroform and acetone in the presence of aqueous sodium hydroxide furnished o-carboxyvinylphenoxyisobutyric acids in good yields. The utility of this new useful protocol was demonstrated by the transformation of the three diesters 9b, 9f and 9g to the sesquiterpenes helianane 4, heliannuol A 2 and heliannuol C 3, respectively.

The synthesis of heliannuol C, an allelochemical from Helianthus annuus

The synthesis of the allelochemical heliannuol C 1 is described by employing a Bargellini condensation and a Claisen rearrangement to install the gem-dimethyl and vinyl functionalities, respectively. A Dieckmann cyclisation of diester 11 enabled the gener