160189-64-0

Upstream product

• 148586-31-6 Acetic acid 2-(2-acetoxy-ethyl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 68548-40-3 5-methoxycarbonyl-5-methoxycarbonylmethyl-bicyclo[2.2.1]heptene 
• 148586-32-7 methyl 6-acetoxy-2-(methoxycarbonyl)-4-methylenehexanoate 
• 148586-33-8 methyl 6-acetoxy-4-methylenehexanoate 
• 160189-62-8 2-(hydroxymethyl)-bicyclo[2.2.1]hept-5-ene-2-ethanol 
• 617-52-7 Dimethyl itakonate 
• 90612-80-9 2-methylene-1,4-butanediol, 1,4-diacetate 
• 160189-63-9 methyl 6-hydroxy-4-methylenehexanoate 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 148586-34-9 methyl 4-methylene-6-(phenylsulfonyl)hexanoate 
• 160189-65-1 4-methylene-6-(phenylsulfonyl)-1-hexanol 
• 148586-30-5 1-<(tert-butyldimethylsilyl)oxy>-4-methylene-6-(phenylsulfonyl)hexane 

Relevant academic research and scientific papers

Total Synthesis of Alternaric Acid

A total synthesis of alternaric acid (1) has been achieved.Key reactions include the Julia olefination of tertiary aldehyde 4 and phenylsulfone 5, and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydropyrone via Fries type rearrangement of O-enola

Total synthesis and stereochemistry of alternaric acid

Determination of the stereochemistry and the total synthesis of alternaric acid 1 has been achieved. The stereostructure of 1 has been elucidated by stereoselective synthesis of four diastereoisomers of the C(9)-C(14) fragment 6, which had been obtained as a degradation product during structural studies. Key reactions of the total synthesis of 1 include the Julia olefination of tertiary aldehyde 6 and phenylsulfone 7 and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydro-2-pyrone via Fries-type rearrangement of the O-enol acyl group of β-keto-δ-valerolactone toward the α-position of the δ-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1. The modified Fries-type rearrangement method has also been extended to the synthesis of some other compounds containing a tricarbonylmethane structure.