87583-72-0

Upstream product

• 87530-47-0 (+/-)-(2,3β,3aβ,8,9,9bα)-hexahydro-3-tert-butyldimethylsilyloxy-3a,6-dimethyl-1H-benzindene-5,7(4H,6H)-dione 
• 83669-69-6 3-(2-furyl)-2-methyl-1-trimethylsiloxy-1-cyclopentene 
• 87530-42-5 (+/-)-(1'β,2'α,3'β)-4-<3'-(2''-furyl)-1'-hydroxy-2'-methylcyclopentan-2'-yl>-1-buten-3-one 
• 87530-48-1 (+/-)-(2,3β,3aβ,5a,8,9,9aβ,9bα)-octahydro-3-tert-butyldimethylsilyloxy-3a,6-dimethyl-1H-benzindene-5,7(4H,6H)-dione 
• 87530-49-2 (+/-)-(2,3β,3aβ,4,8,9,9aβ,9bα)-octahydro-3-tert-butyldimethylsilyloxy-3a,6-dimethyl-5,7-ditrimethylsilyloxy-1H-benzindene 
• 87530-46-9 (3S,3aS,9bS)-3-(tert-Butyl-dimethyl-silanyloxy)-3a-methyl-2,3,3a,4,6,8,9,9b-octahydro-1H-cyclopenta[a]naphthalene-5,7-dione 
• 87530-50-5 (+/-)-(2,3β,3aβ,5aα,8,9,9aβ,9bα)-octahydro-3-tert-butyldimethylsilyloxy-6α-<3'-chlorobut-2'(Z)-en-1'-yl>-3a,6β-dimethyl-1H-benzindene-5,7(4H,6H)-dione 
• 87530-50-5 (+/-)-(2,3β,3aβ,5aα,8,9,9aβ,9bα)-octahydro-3-tert-butyldimethylsilyloxy-6α-<3'-chlorobut-2'(E)-en-1'-yl>-3a,6β-dimethyl-1H-benzindene-5,7(4H,6H)-dione 
• 87530-47-0 (3S,3aS,9bS)-3-(tert-Butyl-dimethyl-silanyloxy)-3a,6-dimethyl-2,3,3a,4,6,8,9,9b-octahydro-1H-cyclopenta[a]naphthalene-5,7-dione 
• 87530-40-3 (Z)-3-Ethoxy-4-((1S,2R)-2-furan-2-yl-1-methyl-5-oxo-cyclopentyl)-but-2-enoic acid ethyl ester 
• 87530-48-1 (3S,3aS,9aS,9bS)-3-(tert-Butyl-dimethyl-silanyloxy)-3a,6-dimethyl-decahydro-cyclopenta[a]naphthalene-5,7-dione 
• 87530-44-7 (+/-)-(1α,2α,5β,6β,9β,11α)-5-tert-butyldimethylsilyloxy-6-methyl-14-oxatetracyclo<7.4.1^1,11.0^2,6>tetradecan-8-one 
• 87530-45-8 (+/-)-(2,3β,3aβ,6,7α,8,9,9bα)-octahydro-3-tert-butyldimethylsilyloxy-7-hydroxy-3a-methyl-1H-benzindene-5(4H)-one 
• 87530-41-4 (1S,2S,3R)-2-((Z)-2-Ethoxy-4-hydroxy-but-2-enyl)-3-furan-2-yl-2-methyl-cyclopentanol 

Downstream Products

• 382-45-6 (+/-)-adrenosterone 

Relevant academic research and scientific papers

INTRAMOLECULAR DIELS-ALDER REACTION WITH FURAN-DIENE. TOTAL SYNTHESIS OF (+/-)-11-KETOTESTOSTERONE AND (+/-)-ADRENOSTERONE.

A novel D BCD ABCD route to 11-keto steroids is reported involving a high yield stereoselective intramolecular Diels-Alder reaction of furan-diene 12 in water as a key-step.The dienophilic side chain is readily introduced starting from 8 via a sequence involving alkylation with ethyl (E)-3-ethoxy-4-iodo-2-butenoate, reduction and acid hydrolysis.The reduced adduct 14 is further converted into (+/-)-adrenosterone (6) via 24, the dienediolate equivalent of which is a known intermediate in corticosteroid synthesis.

INTRAMOLECULAR DIELS-ALDER REACTION WITH FURAN DIENE. A NEW SYNTHESIS OF 11-KETO STEROIDS

A novel D BCD ABCD route to 11-keto steroids is reported involving a high yield stereoselective intramolecular Diels-Alder reaction of furan-diene 5a in water as a key-step.The dienophilic side chain is readily introduced starting from 2 via a sequence involving alkylation with ethyl 4-iodo-3-ethoxycrotonate, reduction and acid hydrolysis.The reduced adduct 8a, obtained in 24 percent overall yield from 2-methyl-1,3-cyclopentanedione, is converted into (+/-)-adrenosterone (16) via base-opening to 9 and further transformation to 13, the dienediolate equivalent of which is a known intermediate in corticosteroid synthesis.