Total Synthesis of (−)-Himandrine
Mohammad Movassaghi, Meiliana Tjandra and Jun Qi
Link to the PDF

So here is a great paper coming out of the Movassaghi Group over at MIT, where I was actually lucky enough to visit once. So the first thing you notice about this paper is the target molecule, a multi-ring, multi-stereocenter compound.

So this paper has plenty of good chemistry: a nice Suzuki, an intramolecular Diels Alder, a Ruthenium cross metathasis, and something Ive never seen, a DDQ oxidation.

They used the Suzuki to construct the diene with the bromo group, leading to the azetidone group addition and the Diels Alder.

The next fun step was the Ru catalyzed cross metathasis. Here they essentially added two carbons and an aldehyde which will be used in an aldol later.

This intermolecular Diels alder sets three stereocenters and closes two rings. A very nice step which is where you can start to begin to see the molecule.

Now for the DDQ oxidation. Here they ran the DDQ in water being a source of oxygen and then the DDQ oxidized the ring to bring forth some enones.

Overall it was a great read and learned alot from it.