696598-49-9

Upstream product

• 100-39-0 benzyl bromide 
• 696598-44-4 (1S,2S,3S)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(1-hydroxy-1-methylethyl)-3-methylcyclobutan-1-ol 
• 100-51-6 benzyl alcohol 
• 696598-39-7 2-{(1R,4S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methyl-2-cyclobutenyl}-2-propanol 
• 697287-54-0 2,2-Dimethyl-propionic acid (S)-6,7-dichloro-1-methyl-4-oxo-3-oxa-bicyclo[3.2.0]hept-2-ylmethyl ester 
• 500777-28-6 (1R,4S,5S)-5-methyl-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]hept-6-en-2-one 
• 84077-32-7 (-)-(S)-4-methyl-5-pivaloyloxymethyl-2(5H)-furanone 

Downstream Products

• 696598-68-2 (1S,5S,6S,8S)-8-benzyloxy-5-(imidazolylthiocarbonyl)-2,2,6-trimethyl-3-oxabicyclo[4.2.0]octan-5-ol 
• 696598-61-5 (1S,5S,6S,8S)-8-benzyloxy-2,2,6-trimethyl-3-oxabicyclo[4.2.0]octan-5-ol 
• 696598-75-1 (1S,6S,8S)-8-benzyloxy-2,2,6-trimethyl-3-oxabicyclo[4.2.0]octane 
• 696598-54-6 (1S)-1-[(1S,2S,3S)-3-(benzyloxy)-2-(1-hydroxy-1-methylethyl)-1-methylcyclobutyl]ethane-1,2-diol 

Relevant academic research and scientific papers

Photochemical cycloaddition of mono-, 1,1-, and 1,2-disubstituted olefins to a chiral 2(5H)-furanone. Diastereoselective synthesis of (+)-lineatin

(Chemical Equation Presented) The photochemical [2 + 2] cycloaddition of (S)-4-methyl-5-O-pivaloyloxymethyl-2(5H)-furanone, 5, to vinyl acetate, vinyl pivalate, tert-butyl vinyl ether, 1,1-diethoxyethylene, and (Z)- and (E)-1,2-dichloroethylene has been studied. A practical synthesis of (+)-lineatin from 5 has been developed via the functionalized cyclobutane 6.

Highly efficient and diastereoselective synthesis of (+)-lineatin

A linear sequence was used to synthesize (+)-lineatin in 14 steps and 14% overall yield from a homochiral 2(5H)-furanone. Key steps of this synthetic approach feature the diastereoselective construction of a cyclobutene through a photochemical [2 + 2] cyc