54192-03-9

Upstream product

• 75-07-0 acetaldehyde 
• 20476-33-9 1α,4α-dibenzyloxy-2α,3α-epoxycyclopentane 
• 131149-29-6 (2R,3S)-2-Hydroxy-5-phenylselanyl-4-((E)-propenyl)-3-(2-trimethylsilanyl-ethoxy)-cyclopentanone 
• 131149-28-5 (+/-)-trans-2-benzeneselenenyl-5-hydroxy-4-(2-trimethylsilylethoxy)-2-cyclopenten-1-one 
• 131149-33-2 5-(E-1-propenyl)-6-(2-trimethylsilylethoxy)-2,3-dihydro-6H-pyran-3-one 
• 126566-35-6 6-(2-trimethylsilylethoxy)-2,3-dihydro-6H-pyran-3-one 
• 126566-40-3 trans-5-hydroxy-4-(2-trimethylsilylethoxy)-2-cyclopenten-1-one 
• 131166-65-9 4-Phenylselanyl-5-((E)-propenyl)-6-(2-trimethylsilanyl-ethoxy)-dihydro-pyran-3-one 
• 131149-31-0 4-benzeneselenenyl-6-(2-trimethylsilylethoxy)-2,3-dihydro-6H-pyran-3-one 
• 81279-58-5 C₁₅H₂₀O₃ 
• 81279-57-4 C₁₃H₁₆O₄ 
• 81279-59-6 C₁₃H₁₄O₂ 
• 81279-62-1 (1R,5R)-4,4-Dimethoxy-2-((E)-propenyl)-6-oxa-bicyclo[3.1.0]hex-2-ene 
• 81279-63-2 (1R,5R)-4,4-Dimethoxy-6-oxa-bicyclo[3.1.0]hex-2-ene-2-carbaldehyde 

Downstream Products

• 582-46-7 (+/-)-terrein 

Relevant academic research and scientific papers

Synthesis and melanin biosynthesis inhibitory activity of (±)-terrein produced by Penicillium sp. 20135

Terrein was isolated from Penicillium sp. 20135, prepared by a practical synthetic way, and evaluated first time for its melanin biosynthesis inhibitory activity. Terrein was isolated from Penicillium sp. 20135, prepared by a practical synthetic way, and evaluated first time for its melanin biosynthesis inhibitory activity.

A total synthesis of racemic and optically active terrein (trans-4,5-dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one)

Two routes to terrein (1), employing a novel ring contraction of 6-alkoxy-2,3-dihydro-6H-pyran-3-ones (5, 13) are described. Separation into enantiomers was carried out by classical resolution via diastereomeric camphanic acid ester intermediates (14, 15)

AN EFFICIENT STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-) TERREIN

Flash vacuum pyrolysis of functionalized tricyclo2,6>decenone epoxide 5, and acetals 3 and 4 affords cyclopentadienone epoxide 6 and acetals 10 and 8, respectively.These epoxides are suitable precursors for the synthesis of (+/-) terrein.