Naturalproductman’s Blog

Hey, is that a natural product?!

Total Synthesis of Himandrine

Posted by naturalproductman on June 25, 2009

Mohammad Movassaghi from MIT has recently published a three paged communication in JACS on the total synthesis of himandrine.  A key highlight of the synthesis includes an intramolecular Diels-Alder with a four-membered enamide-lactam (2-azetidinone group)  substituted on the diene in order to favor the s-cis conformation and also mask the resultant ketone in the natural product.  If you’ve seen his previous synthesis of galbulimima alkaloid GB-13, then you’ll notice that some of the reactions are remniscent of that synthesis.  This molecule is really cool and has good history with Lew Mander being one of the pioneers in the process of discovering this molecule.

himandrine

Did anybody else ever think that Professor Mander looks a little like Professor Larry Overman?  Maybe it’s kind of like how GB-13 looks like himandrine.
larry overman

vs.

Lewis Mander

JACS paper

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4 Responses to “Total Synthesis of Himandrine”

  1. Edinburgher said

    That molecule is a nice compact beastie. The kind of target you want to do a postdoc. Hope to find some spare time to take a look.

    BTW, I love Mander´s work in natural product synthesis.

    • naturalproductman said

      Yeah Mander’s work on galbulimima GB13 was really awesome in JACS a few years back.

      • naturalproductman said

        Speaking of GB13, Sarpong and his grad student, Larson, have recently published in JACS on a total synthesis of galublimima alkaloid 13. Notable reactions include an aryl boronic ester addition onto a ketone using a cationic rhodium catalyst and a complete pyridine to piperidine reduction using rhodium and 1,000 psi of H2.

        paper here

  2. Edinburgher said

    As far as I remember he had a brilliant student doing the molecule.

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