Ley, Bull, Balskus, Horan and Langner. ACIEE, 2006, Early View. DOI: 10.1002/anie.200602050.
A sweet and ultimately, short synthesis of this interesting target. I won’t bore you with a list of biological activity – suffice to say that it’s a very potent anti-fungal agent, and also anthelminthic. Their strategy was based around a unifying and diastereoselective [3+2] nitrile oxide cyclisation. This was used to impart the stereochemistry on one of the “down” via the inside alkoxy effect. The other could then be derived from the reduction of a ketone with Et2BOMe.
This is a thoroughly creative method of generating a 1,3 diol in a stereochemically defined manner, and is well exemplified in this synthesis. They also show two methods of generating a oxazole, one from a amide/aldehyde intramolecular cyclisation which I found particularly interesting.