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Dictyostatin   

11 December 2006 4,476 views 2 Comments

dictyostatin.jpg

Ramachandran, Srivastava and Hazra. Org. Lett. 2006, ASAP. DOI: 10.1021/ol062737k.

Not a lot of new methodology, just a well put together synthesis of Dictyostatin. For the uninitiated, the target is a microtubule stabilizing cancer chemotherapeutic agent, which, unlike paclitaxel, does not bind to P-glycoprotein. This means that the resistance mechanisms operating on this binding mode are inoperative, making this and the related discodermolide increasingly popular targets.

Of course, other syntheses exist, with pioneering work by Paterson and Curran, and a more recent synthesis by Phillips. The approach used by Ramachandran is somewhat similar to those earlier publications, but that’s pretty much unavoidable with certain functionalities. But this is nice work, and as they state in the paper, the overall yield is around 4%; pretty good for this target!

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2 Comments

  • ddd says:

    recently I like glancing through Org Process Research and Development -> section “Some Items of Interest to Process R&D Chemists and Engineers”. A Nice 18 page literature survey of the recently published useful reactions. Last issue
    DOI: 10.1021/op060213u, first page impressive diastereoselective sec-sec-ether sythesis by Merk people

  • yepyep says:

    Well, like I’ve said before I’m not a big macrolide fan, so I read this one quite fast. That means I don’t really have anything useful to contribute to the discussion.

    I noticed, however, that the step 8 -> 11 is not same in the article and in the supporting information. In the article they use Ipc2BH and in the supp info they use Cp2ZrHCl. Also some spelling mistakes here and there, such as Dess-Martin missing one ‘s’ but those are hardly important.