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6-Deoxyerythronolide B   

21 April 2006 3,853 views 2 Comments

6-Deoxyerythronolide B.jpg

Crimmins, and Slade. Org. Lett., 2006, ASAP. DOI: 10.1021/ol0607241

Formal synthesis of 6-Deoxyerythronolide B, using Crimmins aldol methodology (this blog’s turning into Aldol News) to put in eight of the nine stereocentres. Their method revolves around the iterative asymmetric acyl-thiazolidinethione propionate aldol:

6-Deoxyerythronolide B_2.jpg

Getting around 80% yield and >20:1 dr in each of these aldols makes this a pretty sweet job, if a little repetitive.

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2 Comments

  • Klug says:
    21 April, 2006 at 0:46

    All hail the aldol!

    (Great title plate — writing it on the RBF is a nice touch.)

  • Tot. Syn. says:
    21 April, 2006 at 1:01

    Cheers – it sort of looks fake, cause I turned up the saturation to hide the ming at the back of my hood, but it works. All hail photoshop too. If we could combine photoshop and aldol reactions, we could make…ur…yeah.