Total Synthesis of (−)-Himandrine
Author(s)Movassaghi, Mohammad; Tjandra, Meiliana; Qi, Jun
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We describe the first total synthesis of (−)-himandrine, a member of the class II galbulimima alkaloids. Noteworthy features of this chemistry include a diastereoselective Diels−Alder reaction in the rapid synthesis of the tricycle ABC-ring system in an 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 our biogenetically inspired oxidative spirocyclization of an advanced intermediate. The successful and direct late-stage formation of the F-ring in the hexacyclic core of himandrine drew on the power of biogenetic considerations and fully utilized the inherent chemistry of a plausible biosynthetic intermediate.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Journal of the American Chemical Society
American Chemical Society
Movassaghi, Mohammad, Meiliana Tjandra, and Jun Qi. “Total Synthesis of (−)-Himandrine.” Journal of the American Chemical Society 131.28 (2009): 9648-9650.
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