Nicolaou and Harrison. ACIE, 2006, Early View. DOI: 10.1002/anie.200601116
An interesting approach to the abyssomicin family, this time of the C varient. Without getting into the DMDO-related debacle of the Sorensen and Snider papers (though the discrepency is worth a read!), this is an incredibly popular target. Unsurprising, I guess, due to it’s biological profile, but I’m sure we’ll see a few more syntheses before the year is out.
KC’s route uses an impressive DA to put in the six-member ring, generating two stereocentres, in a process somewhat similar to Ward’s. The reaction goes in an impressive 80% yield, leaving a single diastereoisomer. The five member-ring is then created using a Dieckmann cyclisation, and regioselective epoxide opening. Nice end-game too, using RCM (never!), and, um… some interesting conclusions!