59123-24-9

Basic information

• Product Name: (±)-β-apopicropodophyllin
• Synonyms: (±)-β-apopicropodophyllin
• CAS NO: 59123-24-9
• Molecular Weight: 396.397
• Mol File: 59123-24-9.mol

Chemical Properties

• CAS DataBase Reference: (±)-β-apopicropodophyllin(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-β-apopicropodophyllin(59123-24-9)
• EPA Substance Registry System: (±)-β-apopicropodophyllin(59123-24-9)

Safety Data

• Hazardous Substances Data: 59123-24-9(Hazardous Substances Data)

Upstream product

• 7664-93-9 sulfuric acid 
• 477-67-8 (+/-)-isopodophyllinic acid 
• 7732-18-5 water 
• 110-86-1 pyridine 
• 10025-87-3 trichlorophosphate 
• 4375-06-8 epipicropodophyllotoxin 
• 120-57-0 piperonal 
• 33318-75-1 4-benzyl-5-ethoxyoxazole 
• 1338460-64-2 (3-(6-bromobenzo[d][1,3]dioxol-5-yl)prop-1-yn-1-yl)-trimethylsilane 
• 685881-15-6 4-(6-allyl-benzo[1,3]dioxol-5-yl)-4-(3,4,5-trimethoxy-phenyl)-but-2-ynoic acid ethyl ester 
• 477-47-4 Podophyllotoxin 

Downstream Products

• 32384-13-7 (+/-)-α-apopicropodophyllinic acid 

Relevant articles and documents

Synthesis of Cyclic β-Silylalkenyl Triflates via an Alkenyl Cation Intermediate

Trimethylsilylalkyne derivatives are transformed into cyclic β-silylalkenyl triflates through cationic cyclization and subsequent trapping of the alkenyl cation by a triflate anion. β-Silylcyclohexenyl triflates and 3-trimethylsilyl-1,4-dihydronaphth-2-yl

Unusual visible-light photolytic cleavage of tertiary amides during the synthesis of cyclolignans related to podophyllotoxin

During the attempted photochemical cyclization of 2,3-bisbenzylidene-γ-hydroxybutyric acid cyclic amide ester, it was observed that a γ-butyrolactone ring was formed, which was concurrent with the release of the amine fragment from the amide. The process occurs with high yield giving rise to the formation of β-apopicropodophyllin and its regioisomer. Additional experiments confirmed the photochemical nature of this transformation, and that it is independent from the photocyclization of the benzylidene groups – a typical reactivity for the members of the fulgide family. In contrast to the latter UV-driven cyclization, the photochemical cleavage of the amide was proven to proceed under irradiation with visible light.

Rhenium-catalyzed aromatic propargylation

A mild aromatic propargylation reaction, employing an air- and moisture-tolerant rhenium-oxo complex ((dppm)ReOCl3) as a catalyst and a propargyl alcohol as the electrophile, is described. The reaction tolerates a broad range of functional groups and regioselectively affords propargylic arenas without formation of the isomeric allenyl adducts. The potential of this rhenium(V)-catalyzed reaction is exemplified by application of the propargylation to the synthesis of O-methyldetrol, mimosifoliol, and β-apopicropodophyllin.

A New One-Step Preparation of β-Apopicropodophyllin from Podophyllotoxin

β-Apopicropodophyllin (4) has been prepared in one-step in excellent yield by the dehydration of podophyllotoxin (1) with p-toluenesulphonyl chloride in boiling pyridine.