- A direct stereoselective preparation of a fish pheromone and application of the zinc porphyrin tweezer chiroptical protocol in its stereochemical assignment
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A two-step stereoselective preparation of a goldfish pheromone, 17α,20β-dihydroxy-4-pregnen-3-one, is reported from the readily available cortexolone in 64% overall yield. The (20S)-epimer was also synthesized in three steps from cortexolone with an overall yield of 47%. A microscale chiroptical technique based on a host/guest complexation mechanism between the substrate and a dimeric metalloporphyrin host (tweezer) was used to confirm the stereochemical assignment, while Density Functional Theory (DFT) calculations were employed to explain the high stereoselectivity induced by the 17α-hydroxyl and C18-methyl groups. Chirality 00:000-000:, 2013. 2013 Wiley Periodicals, Inc.
- Ouedraogo, Yannick P.,Huang, Longchuan,Torrente, Mariana P.,Proni, Gloria,Chadwick, Ekaterina,Wehmschulte, Rudolf J.,Nesnas, Nasri
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- Simple synthesis of 17α20β-dihydroxypregn-4-en-3-one
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Reduction of 17α-hydroxyprogesterone (1) with NaBH4 produces 17α,20β-dihydroxypregn-4-en-3-one (2) and pregn-4-en-3β,17α,20β-triol (3).
- Kovganko,Kashkan,Shkumatov
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- Oxidation of 17α,20β- and 17α,20α-dihydroxypregn-4- en-3-ones, side products of progesterone biotransformation with recombinant microorganisms expressing cytochrome P-45017α
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Progesterone biotransformation with recombinant yeasts Yarrowia lipolytica E129A15 and Saccharomyces cerevisiae GRF18/YEp5117α expressing bovine adrenocortical cytochrome P-45017α yielded 17α-hydroxyprogesterone and two diols, 17α,20β- and 17α,20α-dihydroxypregn-4-en- 3-ones. The oxidation of mixtures of the three steroids with chromic acid resulted in the cleavage of 17-20 bonds in the diols with the formation of androst-4-ene-3,17-dione. The biotransformation of pregn-4-ene-20β-ol-3-one by means of Y. lipolytica E129A15 was accompanied by the following reactions: the primary oxidation of these compounds to progesterone and the subsequent successive reactions of 17α-hydroxylation and 20α- and 20β-reduction. The results widen the possibilities of enzymatic and chemical modifications of steroids.
- Shkumatov,Usova,Radyuk,Kashkan,Kovganko,Juretzek,Mauersberger
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- A by the 3,17-dione steroid preparing steroid the synthetic method of the compound of
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The invention discloses a synthetic method of steroid type drugs and intermediates, in particular relates to a synthetic method for preparing 17-hydroxy-20-ketone steroid compounds from 3,17-diketone steroids, and belongs to the field of synthesis of drugs. The method takes 3,17-diketone steroids as raw materials and adopts a conventional, environment-friendly, low-toxicity reagent, and the steroid type drugs such as cortisone, hydrocortisone, metacortandracin, or hydroprednisone, or intermediates 17alpha-hydroxy-20-ketone compounds are prepared simply and conveniently at high yield by selective protection of C3 or (and) C11-ketone group, Wittig reaction of C17, selective oxidization of 17(20)-position double bonds and halogenating replacement. The aftertreatment is simple, few three wastes are generated, the reaction selectivity is good, the yield is high, and byproducts anti-pregnancy steroidal drugs and steroidal compounds can be obtained. The raw materials are easy to get, the cost is low and the synthetic process is simple; the synthetic method is suitable for industrial production.
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