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Synfacts 2009(12): 1305-1305
DOI: 10.1055/s-0029-1218327
DOI: 10.1055/s-0029-1218327
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (-)-Himandrine
Contributor(s):Philip KocienskiM. Movassaghi*, M. Tjandra, J. Qi
Massachusetts Institute of Technology, Cambridge, USA
Total Synthesis of (-)-Himandrine
J. Am. Chem. Soc. 2009, 131: 9648-9650
Massachusetts Institute of Technology, Cambridge, USA
Total Synthesis of (-)-Himandrine
J. Am. Chem. Soc. 2009, 131: 9648-9650
Further Information
Publication History
Publication Date:
20 November 2009 (online)
Key words
himandrine - intramolecular Diels-Alder reaction - Suzuki coupling - cross-metathesis - amination - annulation - palladium
Significance
(-)-Himandrine was isolated from the bark of the tree Galbulimima belgraveana. Eight of the ten stereogenic centers were created by diastereoselective processes starting from just two stereogenic centers in fragments B and H.
Comment
The 2-azetidinone moiety at C16 served a dual role: it facilitated the Diels-Alder reaction by providing a 2-N-acylaminodiene E with a greater preference for the s-cis conformation and it served as a latent C16 carbonyl (J → K).