78078-46-3

Upstream product

• 78078-45-2 12-methoxyabieta-2,8,11,13-tetraene 

Downstream Products

• 33465-18-8 salviol 
• 113801-92-6 (4aS,10aR)-7-Isopropyl-6-methoxy-1,1-dimethyl-9-(toluene-4-sulfonyloxy)-1,3,4,9,10,10a-hexahydro-2H-phenanthrene-4a-carboxylic acid methyl ester 
• 24035-36-7 (+/-)-pisiferol 
• 67494-15-9 (+/-)-pisiferic acid 

Relevant academic research and scientific papers

Synthesis of (+)-Hinokiol, (+)-Hinokione, (+)-Salviol, and (+)-2-Oxoferruginol

Reduction of abieta-5,8,11,13-tetraen-3-one with lithium aluminium hydride afforded the corresponding alcohol, which was submitted to catalytic hydrogenation to yield abieta-8,11,13-trien-3β-ol (7) together with its 5βH-isomer.Acetylation of 7, followed by the Friedel-Crafts acylation, afforded 3β-acetoxy-12-acetylabieta-8,11,13-triene.This compound was converted into 3β,12-diacetoxyabieta-8,11,13-triene (11) by the Baeyer-Villiger oxidation.Treatment of 11 with lithium aluminium hydride yielded hinokiol, which was oxidized to hinokione.Subsequently, hinokiol was methylated and the resulting 12-methyl ether was dehydrated to afford 12-methoxyabieta-2,8,11,13-tetraene.The tetraene was then submitted to hydroboration-oxidation to give 12-methoxyabieta-8,11,13-trien-2α-ol (15) which, on demethylation with ethanethiol and anhydrous aluminium chloride, afforded salviol.Oxidation of 15 with pyridinium chlorochromate, followed by demethylation, gave 2-oxoferruginol.