10007-39-3

Upstream product

• 104621-29-6 (8S,9S,10R,13S,14S)-10,13-Dimethyl-17-[1-tripropylsilanyloxy-eth-(Z)-ylidene]-1,6,7,8,9,10,12,13,14,15,16,17-dodecahydro-2H-cyclopenta[a]phenanthrene-3,11-dione 
• 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'(E)-en-1'-yl>-3a,6β-dimethyl-1H-benzindene-5,7(4H,6H)-dione 
• 119830-71-6 C₁₇H₂₂O₃ 
• 119830-74-9 C₁₆H₂₂O₃ 
• 119830-73-8 C₁₆H₂₂O₃ 
• 119804-91-0 3-(1,2-dihydro-4-methoxybenzocyclobutenyl)-1,1-ethylenedioxy-1-isopropenyl-propane 
• 119804-92-1 C₁₆H₂₀O₄ 
• 1120-73-6 2-methyl-2-cyclopenten-1-one 
• 119804-94-3 (3aR,5aR,6S,9aR,9bR)-3a,6-Dimethyl-6-(3-oxo-butyl)-decahydro-cyclopenta[a]naphthalene-3,5,7-trione 
• 564-35-2 (+/-)-11-ketotestosterone 
• 104621-27-4 (3aR,7aS,8S,9R,10aS,10bS,10cS)-9-(tert-Butyl-dimethyl-silanyloxy)-8-isopropenyl-3a,6,7a-trimethyl-1,2,3a,5,7,7a,8,9,10,10a,10b,10c-dodecahydro-4H-cyclopenta[a]phenalen-3-one 
• 1882-86-6 (8S,9R,10R,13S,14S)-17-Acetyl-10,13-dimethyl-1,6,7,8,9,10,12,13,14,15-decahydro-2H-cyclopenta[a]phenanthrene-3,11-dione 
• 104621-21-8 [(1S,2R)-2-Methyl-2-(2-methyl-propenyl)-4-oxo-cyclohexyl]-acetic acid tert-butyl ester 

Relevant academic research and scientific papers

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.

A new strategy for the preparation of 11-oxygenated steroids synthesis of (±)-adrenosterone

Conjugate 1,4-addition of 1-[(tert-butyldimethylsilyl)oxy]-2-methyl- 1,3-cyclohexadiene (5) to 2-methyl-cyclopentenone in highly polar media and subsequent alkylation of the resultant silyl enol ether (4) with phenylthiodienyl carbonate 10 in 5.0 M LiClO4·Et2O provides substrate 2. Exposure of 2 to TMSOTf/TMSOCH2CH2OTMS affords tetracyclic bis-ketal 3, which is converted into (±)-adrenosterone (1) in four steps.

Total Synthesis of ( +/-)-Cortisone. Double-Hydroxylation Reaction for Corticoid Synthesis

Total syntheses of (+/-)-cortisone and (+/-)-adrenosterone have been achieved in 18 steps with the aid of metal-assisted new synthetic sequences in particular, ene reaction and homoenolate chemistry.A novel double-hydroxylation reaction of enol silyl ethers leading to a single step construction of the dihydroxyacetone side chain in corticoids has been developed and applied to the synthesis of cortisone, cortexolone, and 16α-methylcortexolone.

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.