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

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  1. 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


  2. 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
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  3. 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.

  4. 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

  5. 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.
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  6. what's up Beejis?
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