75404-00-1

Upstream product

• 75403-99-5 ethyl 2-(3,4-methylenedioxybenzoyl)-3-(3,4,5-trimethoxyphenyl)-cyclopropanecarboxylate 
• 75403-99-5 ethyl 2-(3,4-methylenedioxybenzoyl)-3-(3,4,5-trimethoxyphenyl)-cyclopropanecarboxylate 
• 1878-29-1 ethyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate 
• 75404-00-1 ethyl rel-(3R,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylate 
• 134310-05-7 4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-3-piperonyloyl-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate 
• 134302-93-5 4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 88775-47-7 (2E)-1-(2H-benzo[3,4-d]1,3-dioxolan-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 64-17-5 ethanol 
• 134302-94-6 3-ethyl 2-methyl rel-(2R,3S,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate 
• 75403-99-5 (2S,3S)-2-(Benzo[1,3]dioxole-5-carbonyl)-3-(3,4,5-trimethoxy-phenyl)-cyclopropanecarboxylic acid ethyl ester 
• 76985-19-8 ethyl 2-(3,4-methylenedioxybenzoyl)-3-(3,4,5-trimethoxyphenyl)-cyclopropanecarboxylate 

Downstream Products

• 75404-00-1 (5S,6R)-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 
• 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 
• 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 
• 106044-49-9 (5S,6S,7S,8R)-7-Cyano-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 106044-47-7 (3aR,4S,5S,10bR)-3-Chloro-5-(3,4,5-trimethoxy-phenyl)-3a,4,5,10b-tetrahydro-1,7,9-trioxa-2-aza-dicyclopenta[a,g]naphthalene-4-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 
• 477-47-4 (+/-) epipodophyllotoxin 
• 106044-41-1 (5S,6S)-5-(3,4,5-Trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid benzhydryl ester 
• 106044-41-1 (5S,6R)-5-(3,4,5-Trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid benzhydryl ester 
• 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 
• 77519-37-0 9-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 112026-14-9 C₂₉H₂₈O₈ 
• 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 

Relevant academic research and scientific papers

Syntheses of (±)-thuriferic acid ethyl ester, its analogues and (±)-picropodophyllone

(±)-Thuriferic acid ethyl ester, its analogues as well as (±)-picropodophyllone have been prepared. The synthetic strategy is based on the utility of vicinal dianions derived from α-aroylsuccinic esters.

Anticancer agent development; 6. Application of the heterocycle annulation-rearrangement strategy in the synthesis of a podophyllotoxin precursor

A four-step synthesis of the Bristol-Myers' precursor, ethyl rel-(3R,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3 ,4-tetrahydronaphthalene-3-carboxylate, to (±)-podophyllotoxin is described in 40% overall yield from ethyl 3,4,5-trimethoxy

TOTAL SYNTHESIS OF (+/-) PODOPHYLLOTOXIN

A straightforward approach to podophyllotoxin was developed using silyl enol ether 5.

Total Synthesis of ( +/-)-Picropodophillone

Following model studies, the synthesis of (+/-)-picropodophillone was completed by first cyclopropanating the appropriate chalcone (11) with ethoxycarbonyl dimethylsulphonium methylide.Treatment of the resulting cyclopropyl ketone with stannic chloride in

Lewis Acid-catalysed Reactions of Aryl Cyclopropyl Ketones. Scope and Mechanism

The effects of aryl substituents on the stannic chloride-catalysed cyclisation of aryl cyclopropyl ketones (1) to aryl tetralones (2) are consistent with the formation of a benzyl carbocation intermediate (8) or a cyclic oxonium ion intermediate (12).The

An Improved Route to an Intermediate in Podophyllotoxin Synthesis

Cyclopropanation of the chalcone (3) with dimethylsulfonium ethoxycarbonylmethylide affords a 1:1 mixture of the cyclopropanyl keto-ester epimers (4) and (5); both stannic chloride and boron trifluoride etherate in nitromethane catalyse the stereoselective cyclisation of this mixture to the tetralone (2), the known podophyllotoxin precursor, in 51percent overall yield.

TRAPPING THE INTERMEDIATE INVOLVED IN THE INTRAMOLECULAR CYCLISATION OF CYCLOPROPYL KETONES. A CONVENIENT PREPARATION OF OPEN-CHAIN γ-HYDROXY KETONES.

The concerted mechanism for the stannic chloride catalysed cyclisation of aryl cyclopropyl ketones is disproved by trapping the intermediate.The reaction provides a facile route to γ-hydroxyketones.