Adrenosterone

Adrenosterone (Reichstein s G) [382-45-6] M 300.4, m 220-224 . Crystd from EtOH. Can be sublimed under high vacuum. 

Adrenergic blocking agents, 241 Adrenergic nervous system, 62 Adrenosterone, 176 Agonists, 20 Aldosterone, 206 Allergen, 41... 

This intramolecular Michael addition has been used to obtain the C/D ring in a short synthesis of adrenosterone (6).2 Thus cyclization of 3 with zirconium tetra-n-propoxide results in the desired 4 and the corresponding cw-isomer in a 25 1 ratio. The B ring was added to give 5 in 62% yield by reaction of the anion of 4 with 2-(trimethylsilyl)-l-pentene-3-one (5, 462). The last ring was then added to obtain 6 by a method developed previously by Stork and Logusch (10,234-235). 

Steroids (hydrocortisone, prednisolone, betamethasone, adrenosterone, fluocortolone,...)... 

Adrenosterone, hydrocortisone, dexamethasone, fluocortolone Apex ODS, 3 pm Acetonitrile-5 mM ammonium acetate in water, gradient from 91 9 to 20 80 240 mm x 50 pm i.d. 160 mm packed length 61... 

Inter- and intramolecular cycloaddition reactions of furans followed by transformation of adducts were employed in the synthesis of complex natural products <02T9903>. As shown below, an intramolecular Diels-AIder reaction served as a key step to set up the D-homo- 10-epi-adrenosterone with non-natural configuration at C-10 <02CEJ1051>. 

Triamcinolone, hydrocortisone, prednidsolone, cortisone, methylprednisolone, betamethasone, dexameth-asone, adrenosterone, fluocortolone, triamcinolone acetonide... 

Figure 10 CEC-UV chromatogram (240 nm) of a mixture of 10 corticosteroids (100 qg/mL) using a linear gradient elution program. Voltage = 30 kV, HPLC injection volume = 10 pL, flow-rate = 10 pL/min for 3 min, then decreased to 100 pL/ min. Gradient program = initial ammonium acetate, 5 mM, in acetonitrile/water (17/83), held for 3 min, then ramped to 38% acetonitrile at 15 min and maintained to end of run. Column = Hypersil ODS, 3 pm, 42 cm total length, 30 cm packed length, 30.1 cm to window, 1 = triamcinolone, 2 = hydrocortisone and prednisolone co-eluting, 3 = cortisone, 4 = methylprednisolone, 5 = betamethasone, 6 = dexamethasone, 7 = adrenosterone, 8 = fluocortolone, 9 = triamcinolone aceto-nide. (Reprinted from Ref. 57, with permission.)...

Stoik et al. have shown that heteroannular extended dienolates such as (73), which contain substituents at both the a- and y-positions, undergo predominantly equatorial alkylation (Scheme 35). The dienolate (73) was product by lithium-ammonia reduction of the tricyclic dienone (72) and the product of its alkylation wiA I-bromo-3-chloro-2-butene and hydrolysis of the resulting enol ether, i.e. (74), was a key intermediate in a short, highly stereoselective synthesis of ( )-adrenosterone. It was pointed out that equatorial alkylation is obtained with dienolates such as (73) and related compounds brcause a peri interaction (Me OMe) of the a- and y-substituents forces the ring a to adopt a half-boat conformation in which the a-face of the ir-system is accessible to attack. 

Reichstein s Substance Fa cortisone. Reichstein s substance G adrenosterone. Reichstein s Substance M l drocortisone. Reichstein s substance Q deoxycortone. Reichstein s substance X aldosterone. 

This reaction was used for a synthesis of the corticosteroid adrenosterone (1), the latter stages of which are shown in equation (II).2... 

Selective oxidation of an allylic secondary alcohol group without attack of saturated secondary alcohol groups was demonstrated by Mancera, Rosenkranz, and Sondheimer. Adrenosterone (I) on reduction with lithium aluminum hydride... 

Adrenosterone (Reichstein s G, androst-4-ene-3,ll,17-trione) [382-45-6] M 300.4, m 214-217 , 220-224 , 224-226 , [a] 1 +364 (c 0.18, EtOH). Dissolve adrenosterone in Me2CO, decolorise it with charcoal, filter, add H2O, Me2CO evaporate and the solid is recrystallised from aqueous EtOH. Also recrystallise it from Et20 or Et20/pentane and dry it at 110 /0.1mm for 2hours. It can be sublimed und high vacuum. [Reichstein Helv Chim Acta 20 953, 979 1937, Mason et al. J Biol Chem 116 267 1936, Beilstein 7 III 4601.]... 

Simultaneous acebutolol, acetazolamide, acetophenetidin, adrenosterone, aldosterone, amitriptyline, androsten-3,17-dione, aspirin, carbamazepine, cephalothin, chlorothiazide, dehydrocorticosterone, deoxycorticosterone, deo cortisol, desipramine, dexamethasone, diazepam, equilenin, estradiol, estriol, estrone, fluorometholone, furosemide, hydrochlorothiazide, hydroxycorticosterone, hydroxyprogesterone, hydroxyprogesterone, imip-ramine, indomethacin, methylhydroxyprogesterone, methylprednisolone, nandrolone, nordiazepam, nortriptyline, pheniramine, phenobarbital, phenytoin, prednisolone, prednisone, primidone, probenecid, progesterone, quinine, spironolactone, testosterone, theophylline, triamcinolone, tripelennamine... 

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