4354-76-1

Usage

Chemical Description

Podophyllotoxin and 4-demethoxypodophylltoxin are compounds that have been studied for their potential as anticancer agents.

InChI:InChI=1/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19+,20-/m0/s1

Upstream product

• 518-28-5 podofilox 
• 13311-04-1 9r-(Tetrahydro-<2>pyranyloxy)-5c-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydro-8H-furo<3',4':6,7>naphtho<2,3-d>(1,3)-dioxol-6-on 
• 75-08-1 ethanethiol 
• 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 
• 106044-42-2 (5R,6R)-5-(3,4,5-Trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 100146-47-2 (5R,6R)-8-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 106044-46-6 (3aS,4R,5R,10bS)-3-Bromo-5-(3,4,5-trimethoxy-phenyl)-3a,4,5,10b-tetrahydro-1,7,9-trioxa-2-aza-dicyclopenta[a,g]naphthalene-4-carboxylic acid benzhydryl ester 
• 75403-99-5 (2S,3S)-2-(Benzo[1,3]dioxole-5-carbonyl)-3-(3,4,5-trimethoxy-phenyl)-cyclopropanecarboxylic acid ethyl ester 
• 1256-91-3 (+/-)-methyl epipodophyllate 
• 120-57-0 piperonal 
• 74879-22-4 6-bromobenzo-1,3-dioxole-5-carboxaldehyde dimethyl acetal 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 103844-26-4 3-hydroxymethyl-6,7-methylenedioxy-4α-t-butylthio-1-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone 
• 477-67-8 (+/-)-isopodophyllinic acid 

Downstream Products

• 59123-24-9 (±)-β-apopicropodophyllin 
• 477-51-0 deoxypicropodophyllotoxin 
• 6559-91-7 (+/-)-4'-O-demethyl-1-epipodophyllotoxin 
• 105655-99-0 1-O-(2-deoxy-2-dimethylamino-β-L-glucopyranosyl)-<(+)-1-epipodophyllotoxin> 
• 105655-99-0 1-O-(2-deoxy-2-dimethylamino-β-D-glucopyranosyl)-<(+)-1-epipodophyllotoxin> 
• 105655-99-0 1-O-(2-deoxy-2-dimethylamino-β-L-glucopyranosyl)-<(-)-1-epipodophyllotoxin> 
• 105655-99-0 1-O-(2-deoxy-2-dimethylamino-β-D-glucopyranosyl)-<(-)-1-epipodophyllotoxin> 
• 112246-50-1 1-O-(β-L-glucopyranosyl)-<(+)-1-epipodophyllotoxin> 
• 112246-48-7 (5S,5aS,8aS,9R)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5-(4-hydroxy-3,5-dimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 112246-49-8 1-O-(β-L-glucopyranosyl)-<(-)-1-epipodophyllotoxin> 
• 112317-52-9 1-O-(2-amino-2-deoxy-β-L-glucopyranosyl)-<(+)-1-epipodophyllotoxin> 
• 112318-79-3 1-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-<(+)-1-epipodophyllotoxin> 
• 112246-51-2 1-O-(2-amino-2-deoxy-β-L-glucopyranosyl)-<(-)-1-epipodophyllotoxin> 
• 92206-82-1 Chloro-acetic acid 4-((5S,5aS,9R)-9-hydroxy-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 

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 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

A SHORT VERSATILE SYNTHESIS OF ARYLTETRALIN LIGNANS INCLUDING DEOXYISOPODOPHYLLOTOXIN AND EPI-ISOPODOPHYLLOTOXIN

Cyclisation of tandem conjugate addition products (10), (15), and (20), prepared by reaction of anions derived from benzyl phenyl and benzyl t-butyl sulphides with but-2-en-4-olide, affords a series of aryltetralin lignans belonging to either the 'normal' or the 'retro' lactone series.Desulphurisation of compound (15) followed by cyclisation, or desulphurisation of the cyclised product (22b), affords deoxyisopodophyllotoxin (5), while treatment of compound (22b) with mercury(II) trifluoroacetate yields epi-isopodophyllotoxin (6).

TOTAL SYNTHESIS OF (+/-)-PODOPHYLLOTOXIN AND (+/-)-EPIPODOPHYLLOTOXIN

A novel approach to (+/-)-epipodophyllotoxin (2c) and hence also to (+/-)-podophyllotoxin (1c) is described, involving as a key-step the stereoselective ring closure of the TMS-ester derived from 17a to the tetralin derivative 30c with mesyl chloride.