173524-35-1

Upstream product

• 151765-80-9 (5R,6R,7S,8S)-7-Formyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 581069-45-6 6.7-Methylendioxy-1-<3.4.5-trimethoxy-phenyl>-1.2-dihydro-naphthoesaeure-(2)-methylester 
• 116097-17-7 3,4-methylenedioxy-6-(3',4',5'-trimethoxybenzoyl)phenylacetic acid 
• 151697-38-0 Acetic acid (5S,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester 
• 151697-36-8 (5R,5aR,6R)-6-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5-carboxylic acid 
• 151697-35-7 C₃₃H₃₈O₁₀ 
• 151697-37-9 (5R,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5-carboxylic acid 
• 116097-18-8 6,7-methylenedioxy-1-(3',4',5'-trimethoxyphenyl)-2-benzopyran-3-one 
• 107401-98-9 Naphtho[2,3-d][1,3]dioxole-6-carbonitrile 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 151697-40-4 (5R,6R,7S,8R)-7-Formyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 581069-48-9 4-isopropyl-2-naphtho[2,3-d][1,3]dioxol-6-yl-4,5-dihydro-oxazole 
• 581069-46-7 (5R,8S)-8-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,8-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 1028264-41-6 3-(3,4,5-trimethoxy-phenyl)-1a,2,3,8b-tetrahydro-1,5,7-trioxa-cyclopenta[g]cyclopropa[a]naphthalene-2-carboxylic acid methyl ester 

Downstream Products

• 1256-91-3 (5R,6R,7R,8R)-methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate 
• 4375-07-9 epipodophyllotoxin 
• 518-28-5 podofilox 

Relevant academic research and scientific papers

Efficient enantioselective total synthesis of (-)-epipodophyllotoxin

In only twelve steps the total synthesis of (-)-epipodophyllotoxin (2) has been completed starting from commercially available piperonal (1). The first stereo-center was formed under auxilary control, while the following epoxidation and radical cyclization proceeded with outstanding diastereoselectivity, which enabled the target molecule to be isolated in an overall yield of 30% and with 97% ee.

Asymmetric total synthesis of (-)-podophyllotoxin

(-)-Podophyllotoxin of 98% optical purity has been synthesized in eight steps and in 15% overall yield. The key step, Diels-Alder addition of the o-quinonoid pyrone 2 [6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2-benzopyran-3-one] to the chiral dienophile 5 [5-(-)-menthyloxyfuran-2(5H)-one], proceeds with very high regio-, endo- and facial selectivity.

Synthesis of Podophyllum Lignans via an Isolable o-Quinonoid Pyrone

The 2-benzopyran-3-one (7) is a stable, isolable, and useful Diels-Alder diene; its adduct (10) formed with dimethyl fumarate is transformed in three steps into methyl epipodophyllate (14) which gives epipodophyllotoxin (2) (81percent) by direct lactonisation (ZnCl2-tetrahydrofuran-4 Angstroem molecular sieves).