133725-65-2

Upstream product

• 133725-63-0 9,12-dimethyl-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindol-6α-ol 
• 98-88-4 benzoyl chloride 
• 133725-55-0 (2S,3S)-5-methyl-3-(1-tosylindol-3-yl)cyclohex-4-ene-1,2-dicarboxylic acid anhydride 
• 121667-71-8 (E)-3-(3-methylbuta-1,3-dienyl)-1-tosylindole 

Downstream Products

• 133725-67-4 6β-(indol-3-yl)-9,12-dimethyl-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole 

Relevant academic research and scientific papers

Antifertility Agents: Synthesis of Yuehchukene Analogues: 6β-(Indol-3-yl)-9,12-dimethyl-6,7,10,11-tetrahydro-7,11-methano-5H-indole and 6β-(Indol-3-yl)-9,12-dimethyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole

Diels-Alder reactions between (E)-3-(3-methylbuta-1,3-dienyl)-1-tosylindole (3) and β-substituted acrylic acid derivatives are described.Reaction of (3) with maleic anhydride afforded the adduct (14).The latter compound in the presence of aluminium trichloride underwent intramolecular acylation with rearrangement to give 9-methyl-6-oxo-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-carboxylic acid (16) and its double bond isomer (17) possessing a skeleton with a close resemblence to that of yuehchukene (1), an antifertility agent.Compounds (16) and (17) were stereoselectively converted into the title compounds (28) and (29).The structures of two precursors, (24) and (25), of compounds (28) and (29) have been determined by X-ray crystallography.