332950-64-8

Upstream product

• 131319-96-5 (+)-(R)-4-Hydroxy-2,2-dimethyl-1-cyclohexanone 
• 123196-48-5 (+)-(4R)-2,2-Dimethyl-4-tetrahydropyranyloxy-1-cyclohexanone 
• 123196-49-6 (S)-6-[1-Hydroxy-meth-(Z)-ylidene]-2,2-dimethyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone 
• 123214-38-0 (+)-(S)-2,2-Dimethyl-6-methylene-4-tetrahydropyranyloxy-1-cyclohexanone 
• 123196-49-6 6-[1-Hydroxy-meth-(Z)-ylidene]-2,2-dimethyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone 
• 123214-38-0 2,2-Dimethyl-6-methylene-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone 
• 123196-50-9 (1'S,4'S)-(Z)-5-(1'-Hydroxy-2',2'-dimethyl-6'-methylene-4'-tetrahydropyranyloxycyclohexyl)-3-methyl-2-penten-5-yl tetrahydropyranyl ether 
• 123196-50-9 (1'R,4'S)-(Z)-5-(1'-Hydroxy-2',2'-dimethyl-6'-methylene-4'-tetrahydropyranyloxycyclohexyl)-3-methyl-2-penten-5-yl tetrahydropyranyl ether 
• 123196-52-1 (-)-(1'R,4'S)-(Z)-5-(1',4'-Dihydroxy-2',2'-dimethyl-6'-methylenecyclohexyl)-3-methyl-2-penten-5-yn-1-ol 
• 123196-48-5 (+/-)-2,2-Dimethyl-4-tetrahydropyranyloxy-1-cyclohexanone 
• 123196-53-2 (2Z,4E)-5-((1S,4S)-1,4-Dihydroxy-2,2-dimethyl-6-methylene-cyclohexyl)-3-methyl-penta-2,4-dienal 
• 123196-51-0 (+)-(1'S,4'S)-(2Z,4E)-5-(1',4'-Diydroxy-2',2'-dimethyl-6'-methylenecyclohexyl)-3-methyl-2,5-pentadien-1-ol 
• 41967-81-1 (Z)-3-Methyl-2-penten-4-ynyl tetrahydropyranyl ether 
• 851040-82-9 (+)-(2Z,4E)-methyl trans-1',4'-dihydroxy-γ-ionylideneacetate 

Relevant academic research and scientific papers

Syntheses of Chiral 4'-Hydroxy and 1',4'-Dihydroxy-γ-ionylideneacetic Acids, Fungal Biosynthetic Intermediates of Abscisic Acid

Both chiral 4'-hydroxy and 1',4'-dihydroxy-γ-ionylideneacetic acids (3, 4 and 5), biosynthetic intermediates of abscisic acid produced by Cercospora cruenta, were synthesized from a chiral starting material, (R)- or (S)-4-hydroxy-2,2-dimethyl-1-cyclohexanone (7). -Sigmatropic rearrangement of (S)-1-chloromethyl-3,3-dimethyl-5-tetrahydropyranyl(THP)oxy-1-cyclohexene (8), followed by the Reformatsky reaction with 4-bromo-3-methyl-2-butenoate (10) gave (1'R,4'S)-4.The diastereomeric isomer, (1'R,4'R)-3, was synthesized in the same manner.The reaction of (S)-2,2-dimethyl-5-methylene-4-THPoxy-1-cyclohexanone (14) with a Grignard reagent prepared from (Z)-3-methyl-2-penten-4-ynyl THP ether (15) and subsequent conversion of the side chain gave (1'S,4'S)-5.These synthetic compounds confirmed the stereochemistry of natural 3, 4 and 5.