247067-76-1

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 247067-74-9 3β-(tert-butyldimethylsilyloxy)-14α,20ξ-card-5-enolide 
• 247067-73-8 3β-(tert-butyldimethylsilyloxy)-24-nor-21,23-cyclochol-5-en-23-one 
• 247067-71-6 3β-acetoxy-24-nor-21,23-cyclochol-5-en-23-one 
• 247067-72-7 3β-hydroxy-24-nor-21,23-cyclochol-5-en-23-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 72560-37-3 3-O-acetylpregna-5,20-dien-3β-ol 

Relevant academic research and scientific papers

Cyclobutanone approach to the synthesis of cardenolides

17β-(3′-Oxocyclobutyl)androstane, prepared by the thermal [2 + 2] cycloaddition of dichloroketene to 3β-acetoxypregna-5,20-diene, is the key intermediate in the new, efficient synthesis of steroids bearing the 17β-butenolide fragment that characterizes cardenolides. The six-step synthesis of 3β-tert-butyldimethylsilyloxy-14α-carda-5,20(22)- dienolide was achieved with a total yield of 32%. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

A new approach to the synthesis of the 17β-butenolide fragment of cardenolides

A new, efficient synthesis of the 17β-butenolide fragment characteristic of cardenolides is effected by [2 + 2]-cycloaddition of dichloroketene to 3β-acetoxypregna-5,20-diene, as a key step.