17187-81-4

Basic information

• Product Name: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5R-(5a,5aa,8ab)]- (9CI)
• Synonyms: Isopodophyllotoxin,4-deoxy-, (+)- (8CI); (+)-Isodeoxypodophyllotoxin; Isodesoxypodophyllotoxin;NSC 332045
• CAS NO: 17187-81-4
• Molecular Formula: C22H22 O7
• Molecular Weight: 398.412
• Mol File: 17187-81-4.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 564.5°Cat760mmHg
• Flash Point: 247°C
• Density: 1.304g/cm³
• CAS DataBase Reference: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5R-(5a,5aa,8ab)]- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5R-(5a,5aa,8ab)]- (9CI)(17187-81-4)
• EPA Substance Registry System: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5R-(5a,5aa,8ab)]- (9CI)(17187-81-4)

Safety Data

• Hazardous Substances Data: 17187-81-4(Hazardous Substances Data)

Upstream product

• 75-11-6 diiodomethane 
• 1173-42-8 6,7-demethylenedeoxypodophyllotoxin 
• 24150-39-8 deoxypicropodophyllin 
• 103844-17-3 2-(α-hydroxy-3',4',5'-trimethoxybenzyl)-3-(3'',4''-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone 
• 1254-07-5 7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 74879-22-4 6-bromobenzo-1,3-dioxole-5-carboxaldehyde dimethyl acetal 
• 17187-78-9 (3S,4R)-4-Benzo[1,3]dioxol-5-ylmethyl-3-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one 
• 17187-78-9 (3R,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one 
• 75101-87-0 dimethyl 1,4-epoxy-1,2,3,4-tetrahydro-6,7-(methylenedioxy)-1-(1,2-cis)-(3',4',5'-trimethoxyphenyl)-2,3-trans-naphthalenedicarboxylate 
• 75101-87-0 dimethyl 1,4-epoxy-1,2,3,4-tetrahydro-6,7-(methylenedioxy)-1-(1,2-cis)-(3',4',5'-trimethoxyphenyl)-2,3-cis-naphthalenedicarboxylate 
• 76886-74-3 C₂₄H₂₂O₁₀ 
• 75101-88-1 methyl 1,4-epoxy-3-exo-(hydroxymethyl)-6,7-(methylenedioxy)-1-(1,2-cis)-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2-endo-carboxylate 
• 1256-91-3 (+/-)-methyl epipodophyllate 

Downstream Products

• 117097-50-4 (-)-(1R,2S,3S)-1-(3,4,5-trimethoxyphenyl)-2-(methoxycarbonyl)-3-<<(tert-butyldimethylsilyl)oxy>methyl>-6,7-(methylenedioxy)-2,3-dihydro-4(1H)-naphtalenone 
• 55515-11-2 isodeoxypodophyllinic acid methyl ester 
• 6258-41-9 5-(3,4,5-Trimethoxy-phenyl)-8H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 93108-14-6 2'-bromo-demethylene-desoxypodophyllotoxin 
• 140147-76-8 deoxypicropodophyllinic acid methyl ester 
• 171483-28-6 (5R,6S,7R)-7-Formyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 25088-82-8 9-deoxyanhydropodophyllol 
• 321747-15-3 C₂₂H₂₄O₇ 
• 321747-09-5 deoxyanhydro-4-isopodophyllol 

Relevant articles and documents

Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans

(?)-Podophyllotoxin is one of the most potent microtubule depolymerizing agents and has served as an important lead compound in antineoplastic drug discovery. Reported here is a short chemoenzymatic total synthesis of (?)-podophyllotoxin and related aryltetralin lignans. Vital to this approach is the use of an enzymatic oxidative C?C coupling reaction to construct the tetracyclic core of the natural product in a diastereoselective fashion. This strategy allows gram-scale access to (?)-deoxypodophyllotoxin and is readily adaptable to the preparation of related aryltetralin lignans.

Divergent Asymmetric Syntheses of Podophyllotoxin and Related Family Members via Stereoselective Reductive Ni-Catalysis

A nickel-catalyzed reductive cascade approach to the efficient construction of diastereodivergent cores embedded in podophyllum lignans is developed for the first time. Their gram-scale access paved the way for unified syntheses of naturally occurring podophyllotoxin and other members.

Synthesis and Computational Studies Demonstrate the Utility of an Intramolecular Styryl Diels-Alder Reaction and Di-t-butylhydroxytoluene Assisted [1,3]-Shift to Construct Anticancer dl-Deoxypodophyllotoxin

Deoxypodophyllotoxin is a secondary metabolite lignan possessing potent anticancer activity with potential as a precursor for known anticancer drugs, but its use is limited by scarcity from natural sources. We here report the total synthesis of racemic de