17a hydroxy-pregna-1 4-diene-3 20-dione

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  1. Oooo, i love candy!!


  2. I meant reaction with Sodium bismuthate to make androstenedione and androstadiendione
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  3. Quote Originally Posted by YoungJD View Post
    I meant reaction with Sodium bismuthate to make androstenedione and androstadiendione
    that may acheive side chain clevage to give the latter compound. i am not sure
    Anabolicminds.com Featured Author

  4. Good Morning, Patrick.
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  5. Quote Originally Posted by Patrick Arnold View Post
    that may acheive side chain clevage to give the latter compound. i am not sure
    What side chain?

    I know it's apparently a stronger oxidant than KMnO4, I just don't think it exhibits SET behavior. You'd probably have MUCH better luck using Nicolaou's IBX protocol... IDK, say, 4eq IBX in DMSO, 2d at 80*C inside the vessel ought to do the trick
    E-Pharm Nutrition Representative
    WARNING: I tend to speak my mind and will verbally assault you if you are a tool. My words do not necessarily represent the official opinion of E-Pharm, but most likely, they do.

  6. the pregnane side chain.

    it usually requires previous reduction of the 20-keto group though

    we have done this before. we were trying to make 4-dhea starting from 17a-hydroxyprogesterone at one time. lead tetraacetete worked better, but the amount of lead left in the final product was troubling
    Anabolicminds.com Featured Author

  7. Quote Originally Posted by Beejis60 View Post
    What side chain?

    I know it's apparently a stronger oxidant than KMnO4, I just don't think it exhibits SET behavior. You'd probably have MUCH better luck using Nicolaou's IBX protocol... IDK, say, 4eq IBX in DMSO, 2d at 80*C inside the vessel ought to do the trick

    IBX unfortunately tends to cause dehydrogenation reactions. u would end up with a considerable amount of 4,6
    Anabolicminds.com Featured Author

  8. u should try to find a copy of carl djreassi's "steroid reactions" beejis
    Anabolicminds.com Featured Author

  9. Quote Originally Posted by Patrick Arnold View Post
    the pregnane side chain.

    it usually requires previous reduction of the 20-keto group though

    we have done this before. we were trying to make 4-dhea starting from 17a-hydroxyprogesterone at one time. lead tetraacetete worked better, but the amount of lead left in the final product was troubling
    Wasn't he talking about from androstenedione? Amihigh?

    Quote Originally Posted by Patrick Arnold View Post
    IBX unfortunately tends to cause dehydrogenation reactions. u would end up with a considerable amount of 4,6
    Not with androstenedione as an SM... or even androstanedione JACS, 2002, 124(10), 2245. I've memorized all the Nicolaou/Baran IBX papers. This one is a particularly tricky reaction, but doable.

    Quote Originally Posted by Patrick Arnold View Post
    u should try to find a copy of carl djreassi's "steroid reactions" beejis
    three american dollars plus shipping? I'll take two.
    E-Pharm Nutrition Representative
    WARNING: I tend to speak my mind and will verbally assault you if you are a tool. My words do not necessarily represent the official opinion of E-Pharm, but most likely, they do.

  10. Quote Originally Posted by Beejis60 View Post
    Wasn't he talking about from androstenedione? Amihigh?
    .
    i dunno, i thought he was talking about from 17a-OHP
    Anabolicminds.com Featured Author

  11. Quote Originally Posted by Beejis60 View Post


    Not with androstenedione as an SM... or even androstanedione JACS, 2002, 124(10), 2245. I've memorized all the Nicolaou/Baran IBX papers. This one is a particularly tricky reaction, but doable.


    .
    U do recall that IBX in dmso was the method we used to make 1-ad (first step)

    It was a very nice reaction. It would give small amounts of 4-dione and 1,4-dione as side products though.

    It was much easier than the way we first made the product, which involved a bromination step followed by a debromination step
    Anabolicminds.com Featured Author

  12. Quote Originally Posted by Patrick Arnold View Post
    U do recall that IBX in dmso was the method we used to make 1-ad (first step)

    It was a very nice reaction. It would give small amounts of 4-dione and 1,4-dione as side products though.

    It was much easier than the way we first made the product, which involved a bromination step followed by a debromination step
    At longer temps and a twat hair of water to initiate the 'enol' IBX form, conversion of androstanedione and androstenedione proceeds nicely to boldione. I guess I missed whatever you were talking about. Don't think I've ever seen anyone use bismuthate for oxidative cleavage though. Phil Baran blows out the 17-side chain of prednisone (similar steroidal structure to OHP) with NaIO4 quite nicely in his synthesis of Cortistatin A.
    E-Pharm Nutrition Representative
    WARNING: I tend to speak my mind and will verbally assault you if you are a tool. My words do not necessarily represent the official opinion of E-Pharm, but most likely, they do.

  13. Quote Originally Posted by Beejis60 View Post
    At longer temps and a twat hair of water to initiate the 'enol' IBX form, conversion of androstanedione and androstenedione proceeds nicely to boldione. I guess I missed whatever you were talking about. Don't think I've ever seen anyone use bismuthate for oxidative cleavage though. Phil Baran blows out the 17-side chain of prednisone (similar steroidal structure to OHP) with NaIO4 quite nicely in his synthesis of Cortistatin A.
    there is a whole section on conversion of 20-ketosteroids to 17-ketosteroids in the djerassi book i mentioned.

    we used jones reagent in acetone to make the adrenosterone from hydrocortisone. If cortisone were commercially available we could have used a milder oxidizing reagent
    Anabolicminds.com Featured Author

  14. Interesting that Jones Ox cleaves that side chain. Probably a bit cheaper than IBX but probably not as 'innocuous' as NaIO4. Can't imagine a ton of con. H2SO4 and CrO3 being cheap, safe, and "green". The workup of Jones Ox is beautiful though.
    Ordered that book at a solid $3.35. Gonna be my 2nd favorite book behind Dehydrobenzene and Cycloalkynes by Hoffmann.
    E-Pharm Nutrition Representative
    WARNING: I tend to speak my mind and will verbally assault you if you are a tool. My words do not necessarily represent the official opinion of E-Pharm, but most likely, they do.

  15. what's up Beejis?
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