119139-56-9

Upstream product

• 170241-30-2 12-benzoyloxy-3-hydroxy-5,10-friedo-4,5-seco-abieta-5⁽¹⁰⁾,6,8,12-tetraene-11,14-dione 
• 181871-21-6 1,3,4-triacetoxy-5-(3-acetoxy-4-methylpentyl)-2-isopropyl-6-methylnaphthalene 
• 181871-20-5 5-(3-acetoxy-4-methylpentyl)-2-isopropyl-6-methyl-3,4-naphthoquinone 
• 181871-18-1 5-(3-acetoxy-4-methylpentyl)-2-isopropyl-3-methoxy-6-methylnaphthalene 
• 181871-19-2 5-(3-acetoxy-4-methylpentyl)-2-isopropyl-6-methyl-3-naphthol 
• 181871-16-9 2-isopropyl-3-methoxy-6-methyl-5-(4-methyl-3-oxopentyl)naphthalene 
• 181871-17-0 5-(3-hydroxy-4-methylpentyl)-2-isopropyl-3-methoxy-6-methylnaphthalene 
• 181871-22-7 3-hydroxy-5-(3-hydroxy-4-methylpentyl)-2-isopropyl-6-methyl-1,4-naphthoquinone 
• 170241-31-3 12-benzoyloxy-5,10-friedo-4,5-seco-abieta-5⁽¹⁰⁾,6,8,12-tetraene-3,11,14-trione 

Relevant academic research and scientific papers

A new synthesis of 3-oxosapriparaquinone, a diterpene from Salvia prionitis HANCE (Labiatae)

5,8,11,13-Abietatetraen-3-one (3) and its 12-methoxy derivative (7) were oxidized to the corresponding 3,7-diones, which were rearranged respectively into 2-isopropyl-6-methyl-5-(4-methyl-3-oxopentyl)naphthalene (6) and its 12-methoxy derivative (10) by sodium borohydride reduction and subsequent dehydration with boron trifluoride etherate. Compound 10 was further converted into 3-oxosapriparaquinone (1) via 5-(3-acetoxy-4- methylpentyl)-2-isopropyl-6-methyl-3,4-naphthoquinone (14).

Synthesis of 3-oxosapriparaquinone, a diterpene from Salvia prionitis hance

12-Acetoxy-5,16-friedo-4,5-seco-abieta-3,5(10),6,8,11,13-hexaene prepared from (+)-dehydroabietic acid, was converted into a natural rearranged abietane-type diterpene, 3-oxosapriparaquinone, via 12-benzoyloxy-3-hydroxy-5,10-friedo-4,5-seco-abieta-5(10),6,8,12-tetra ene-11,14-dione by a series of reactions: hydroboration-oxidation, benzoyl peroxide oxidation, Jones oxidation, and alkaline hydrolysis.