77519-37-0

Upstream product

• 104715-48-2 (5S,6S,7S,8S)-7-Aminomethyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 79289-93-3 (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid 
• 79305-58-1 (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid methyl ester 
• 1256-91-3 (+/-)-methyl epipodophyllate 
• 1256-91-3 methyl isopicropodophyllate 
• 75101-88-1 C₂₃H₂₄O₉ 
• 79305-58-1 methyl epipodophyllate 4,11-acetonide 
• 79289-93-3 epipodophyllic acid 4,11-acetonide 
• 116097-18-8 6,7-methylenedioxy-1-(3',4',5'-trimethoxyphenyl)-2-benzopyran-3-one 
• 106044-42-2 (5R,6R)-5-(3,4,5-Trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 104715-48-2 (5S,6S,7S,8R)-7-Aminomethyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 112026-13-8 (5S,6S,7S)-7-Benzyloxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester 
• 112026-14-9 C₂₉H₂₈O₈ 
• 112026-12-7 (5S,6S)-5-(3,4,5-Trimethoxy-phenyl)-8-trimethylsilanyloxy-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester 

Downstream Products

• 59123-24-9 (±)-β-apopicropodophyllin 
• 477-51-0 deoxypicropodophyllotoxin 
• 33419-42-0 etoposide 
• 112146-42-6 4′-demethyl-(epi)-podophyllotoxin 4-O-2″-deoxy-2″-amino-4″,6″-di-O-ethylidene-β-D-glucopyranoside 
• 131118-85-9 {(2R,4aR,6R,7R,8R,8aS)-8-Hydroxy-6-[(5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy]-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester 
• 131118-85-9 {(2S,4aS,6S,7S,8S,8aR)-8-Hydroxy-6-[(5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy]-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester 
• 131118-85-9 {(2R,4aR,6R,7R,8R,8aS)-8-Hydroxy-6-[(5R,5aS,8aS,9S)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy]-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester 
• 131118-85-9 {(2S,4aS,6S,7S,8S,8aR)-8-Hydroxy-6-[(5R,5aS,8aS,9S)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy]-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester 
• 92206-80-9 1-O-(2,3-di-O-chloroacetyl-4:6-O-ethylidene-β-D-glucopyranosyl)-<(-)-4'-O-chloroacetyl-1-epipodophyllotoxin> 
• 92206-80-9 Chloro-acetic acid 4-{(5R,5aR,8aR,9S)-9-[(2S,4aS,6S,7S,8R,8aS)-7,8-bis-(2-chloro-acetoxy)-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl}-2,6-dimethoxy-phenyl ester 
• 92206-80-9 1-O-(2,3-di-O-chloroacetyl-4:6-O-ethylidene-β-D-glucopyranosyl)-<(+)-4'-O-chloroacetyl-1-epipodophyllotoxin> 
• 92206-80-9 Chloro-acetic acid 4-{(5S,5aS,8aS,9R)-9-[(2S,4aS,6S,7S,8R,8aS)-7,8-bis-(2-chloro-acetoxy)-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl}-2,6-dimethoxy-phenyl ester 
• 112146-51-7 1-O-(2-benzyloxycarbonylamido-3-chloroacetyl-2-deoxy-4:6-O-ethylidene-β-D-glucopyranosyl)-<(-)-4'-O-chloroacetyl-1-epipodophyllotoxin> 
• 112146-51-7 C₄₁H₄₁Cl₂NO₁₆ 

Relevant academic research and scientific papers

Silenes in organic synthesis: A concise synthesis of (±)-epi- picropodophyllin

A concise, seven step synthesis of the aryl tetralin lignan lactone epi-picropodophyllin from piperonal is described. The key steps are a silene diene Diels-Alder reaction and the Hosomi-Sakurai reaction of the resultant silacyclohexene. The Royal Society

A new and efficient strategy for the synthesis of podophyllotoxin and its analogues

Figure presented An efficient and stereoselective strategy for the total synthesis of podophyllotoxin was developed. This route leads to podophyllotoxin 1 in only 12 steps with 29% overall yield. A notable feature of this synthetic strategy is the use of

A concise stereocontrolled formal total synthesis of (+/-)-podophyllotoxin using sulfoxide chemistry.

A short stereoselective formal total synthesis of (+/-)-podophyllotoxin has been carried out from a sulfoxide, using a one-pot tandem conjugate addition/aldol/electrophilic aromatic substitution reaction to form a tetralin, which was converted into picrop

A Mild Method for Selective Cleavage of Tetrahydropyranyl Ethers in the Presence of Other Acid-Labile Functionalities

A mild method for selective cleavage of tetrahydropyranyl ethers in the presence of other acid sensitive functionalities such as acetonides, methoxymethyl ethers, methylenedioxy ethers, mesitylaldehyde acetals and t-butyldimethylsilyl ethers using Lewis acid-thiol system is described.

Synthesis of Podophyllum Lignans via an Isolable o-Quinonoid Pyrone

The 2-benzopyran-3-one 10 is a stable, isolable and useful Diels-Alder diene; its methyl 4-benzoyloxycrotonate adduct 23 formed regioselectively and stereoselectively in acetonitrile is reduced with H2/Pd to give 31 with inversion of C-1 stereochemistry.T

Synthesis of (+/-)-4-Deoxypodophyllotoxin, (+/-)-Podophyllotoxin and (+/-)-Epipodophyllotoxin

6,7-Methylenedioxy-1-(3',4',5'-trimethoxyphenyl)-2-benzopyran-3-one 1 and dimethyl fumarate in acetonitrile give mostly the C-2 exo-CO2Me adduct 4 which is transformed in four steps into epipodophyllotoxin 10a.Attempted addition of dimethyl maleate to 1 p

Comprehensive Synthetic Route to Eight Diastereomeric Podophyllum Lignans

An oxabicyclo compound, 9, prepared in 47percent yield through an isobenzofuran intermediate was converted with excellent regio- and stereocontrol to eight (+/-)-lignan lactones of the podophyllotoxin series.One of the eight, epiisopicropodophyllin, 36, t

Synthesis of Podophyllotoxin

The alkene (2) obtained directly from the reaction of dimethyl maleate with the pyrone (1) is converted into (+/-)-podophyllotoxin (12) in seven steps and 24percent overall yield; novel steps include the epimerisation of (9) at C-3 using 1,8-diazabicyclo

A Highly Stereoselective Synthesis of Podophyllotoxin and Analogues Based on an Intramolecular Diels-Alder Reaction

A synthesis of podophyllotoxin and several analogues is described.The key step that generates all four chiral centers of podophylotoxin involves an intramolecular Diels-Alder reaction between an appropriately substituted o-quinodimethane and a pendant cro