139386-19-9

Upstream product

• 94-36-0 dibenzoyl peroxide 
• 89471-30-7 (R)-9-Acetyl-6-hydroxy-7-isopropyl-3-(3-methoxypropyl)-3,4-dimethylnaphtho<2,3-b>furan-2(3H)-one 

Downstream Products

• 139386-21-3 (R)-9-Acetyl-6-benzoyloxy-7-isopropyl-3-(3-methoxypropyl)-3,4-dimethylnaphtho<2,3-b>furan-2,5,8(3H)-trione 
• 139386-20-2 (R)-9-Acetoxy-6-benzoyloxy-7-isopropyl-3-(3-methoxypropyl)-3,4-dimethylnaphtho<2,3-b>furan-2,5,8(3H)-trione 

Relevant academic research and scientific papers

Chemical transformation of (+)-dehydroabietic acid leading to a formal synthesis of (+)-coleon A

(R)-6-Hydroxy-7-isopropyl-3-(3-methoxypropyl)-3,4-dimethylnaphtho[2,3-b ]furan-2(3H)-one (3), prepared from (+)-dehydroabietic acid (2), was converted into (R)-9-acetoxy-6-benzoyloxy-7-isopropyl-3-(3-methoxypropyl)-3,4-dimethyl naphtho[2,3-b]furan-2,5,8(3H)-trione (10) and its 9-acetyl compound (11) by a series of reactions: sodium borohydride reduction, acetylation, alkaline hydrolysis, benzoyl peroxide oxidation, Jones oxidation, and m-chloroperbenzoic acid oxidation. The trione 10 was further transformed into (R)-5,6,8,9-tetraacetoxy-7-isopropyl-3(3-methoxypropyl)-3,4-dimethylnap htho[2,3-b]furan-2(3H)-one (15) by alkaline hydrolysis and reductive acetylation. Since the conversion of 15 into coleon A (1) has already been reported, the present work can be regarded as a new formal synthesis of coleon A.