24684-50-2

Upstream product

• 17521-83-4 3-methoxy-6,7,16,17-tetrahydro-15H-cyclopenta-phenanthren-17-one 
• 792-07-4 3-methoxy-16,17-dihydro-15H-cyclopenta-phenanthren-17-one 

Downstream Products

• 143216-79-9 15,16-dihydro-3-hydroxycyclopentaphenanthren-17-one methoxime 
• 145628-92-8 3-(Benzoyloxy)-15,16-dihydrocyclopentaphenanthren-17-one 
• 143290-36-2 3,4,15,16-tetrahydro-trans-3,4-dihydroxycyclopentaphenanthren-17-one 
• 145628-94-0 Benzoic acid 17-hydroxy-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-yl ester 
• 150711-22-1 17-(tert-Butyl-diphenyl-silanyloxy)-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-ol 
• 145629-00-1 17-<(tert-Butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene-3,4-dione 
• 145628-96-2 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene 
• 143216-81-3 (3S,4S)-3,4-Dihydroxy-3,4,15,16-tetrahydro-cyclopenta[a]phenanthren-17-one O-methyl-oxime 
• 143216-80-2 15,16-dihydrocyclopentaphenanthren-3,4,17-trione 17-methoxime 
• 143216-84-6 (+/-)-2α-bromo-1,2,3,4,15,16-hexahydro-trans-1β,3α,4β-trihydroxycyclopentaphenanthren-17-one 
• 143216-83-5 3,4,15,16-tetrahydro-trans-3,4-bis<(tert-butyldimethylsilyl)oxy>cyclopentaphenanthren-17-one 
• 143216-82-4 3,4,15,16-tetrahydro-trans-3,4-bis<(tert-butyldimethylsilyl)oxy>cyclopentaphenanthren-17-one methoxime 

Relevant academic research and scientific papers

Synthesis of the trans-3,4-Dihydrodiol Metabolites of the Steroid-Related Carcinogen 15,16-Dihydrocyclopentaphenanthren-17-one and Its 11-Methyl Derivative

Cyclopentaphenanthrenes are a class of carcinogenic polycyclic aromatic hydrocarbons that are structurally related to steroids.Optimum tumorigenic activity is associated with a methyl group in the 11-position and a keto group in the 17-position.Synthes

Synthesis of the Putative Active Metabolites of the Cyclopentaphenanthrenes. Synthesis of the trans-3,4-Dihydro 3,4-Diol and syn-3,4-Diol 1,2-Epoxide Derivatives of the Mutagen 15,16-Dihydrocyclopentaphenanthren-17-one

The first synthesis of the trans-dihydro diol and syn-diol epoxide derivatives of a biologically active cyclopentaphenanthrene is described.The cyclopentaphenanthrene skeleton is rapidly and efficiently assembled utilizing the Lewis acid-catalyzed Diels-Alder reaction of 1,2-dihydro-7-methoxy-4-vinylnaphthalene (5) with an α-heterosubstituted cyclopentenone, a "cyclopentynone" equivalent.It was found that the Diels-Alder reaction of α-(phenylselenenyl)- (6a) or α-bromocyclopentenone (6b) with 5 in the presence of 1.5 equiv of SnCl4 followed by elimination with hydrogen peroxide or DBU produced the key intermediate 15,16-dihydro-3-methoxycyclopentaphenanthren-17-one (10) in 28percent or 59percent overall yield, respectively.The synthesis of the A-ring metabolites features the use of a unique methoxime protecting group for the 17-ketone.The deprotection of the 17-methoxime group of the highly acid-sensitive 3,4-trans-dihydro 3,4-diol bis(TBDMS) ether 15b was achieved through the use of the low-valent titanium reagent produced upon reduction of TiCl3-3THF by DIBAL-H (51percent).Treatment of bis-(TBDMS) ether 16 with TBAF in THF provided the desired 3,4-trans-dihydro 3,4-diol (3) (83percent), thus achieving the synthesis of 3 in 10 steps in 9.6percent overall yield from 6b.In addition, the bay-region syn-3,4-diol 1,2-epoxide (4a) was also synthesized from 3 in two steps in 59percent overall yield.