Meiliana Tjandra and Dr. Jun Qi in the Movassaghi group have completed the first total synthesis of (–)-himandrine. Their synthesis features a diastereoselective Diels-Alder reaction in the rapid synthesis of the tricycle ABC-ring system in enantiomerically enriched form, the use of a formal [3+3] annulation strategy to secure the CDE-ring system with complete diastereoselection, and successful implementation of their biogenetically inspired oxidative spirocyclization of an advanced intermediate. The successful and direct late-stage formation of the spirofused BF-rings in the hexacyclic core of himandrine drew on the power of biogenetic considerations and fully utilized the inherent chemistry of a plausible biosynthetic intermediate.

More News>>