Epi androsterone

A series of conjugated polyenes capped with chromophores and containing an androstane spacer were synthesized by Wittig or Wittig-type olefinations from epi-androsterone 5150. For example, vinyl carboxaldehyde 52, prepared from 51 in 60% yield as shown in equation 32, was treated with 9-anthrylmethylphosphonium bromide and n-butyllithium to give diene 53. Exocyclic diene 53 was subsequently oxidized to vinyl carboxaldehyde 54. The androsterone vinyl aldehyde intermediate could either be treated with a tetraphenylporphyrinpolyenyl phosphonium ylide, or, as shown below, the phosphonium salt of the androsterone (55) could be reacted with TPP polyeneal 56. The desired all-(E) isomer, 57, was obtained from the ( )/(Z)-isomeric mixture by chromatographic purification. 

Although it has been stated that only phenols are conjugated with sulfuric acid,1 three urinary steroid sulfate esters (androsterone sulfate, dehydro-epi-androsterone sulfate, and A 6-aZZo-pregnene-3(/3)-ol-20-one sulfate) have been isolated in which the sulfuric acid is esterified by an alcoholic hydroxyl group.111 It is true that no alcohol administered to... 

Dehydro-epi-androsterone Sodium hydroxide Oenanthic acid anhydride... 

A mixture of 10.0 g of dehydro-epi-androsterone, 40 ml of pyridine and 20 ml of oenanthic acid anhydride was warmed for 2 h on a steam bath. About 10 ml of water were added and the mixture was warmed for a further 30 min. The reaction mixture was then subjected to a steam distillation. The resulting mixture was extracted with ether and the extract was successively washed with dilute sodium hydroxide solution, sodium carbonate solution and water. 

Figure 2. Low resolution (/ = 1000) spectrum of dehydro-epi-androsteron. direct inlet using a VG 7070E. electron impact mass spectrometer (ElMS)...

Glucose 6PDH overexpression 6-aminonicotinamide (6-AN), epi-androsterone and dihydroepiandrosterone (DHEA)... 

The prefix alio- is a term used to describe tlie stereoisomerism of the hydrogen atom at C-5. When the configuration differs at any other carbon atom, the prefix epi- is used (e.g., androsterone possesses a 3a-hydroxyl group, and epiandrosterone a 3P-hydroxyl group testosterone possesses a 17P-hydroxyl group, and epitestosterone a 17a-hydroxyl group).. 

Androsterone (m.p. 185°C) is anatnrally occurring androgen that may be isolated from male urine. It can also be synthesized from epi-cholestanyl acetate as given below ... 

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