Synfacts 2009(12): 1305-1305  
DOI: 10.1055/s-0029-1218327
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Himandrine

Rezensent(en):Philip Kocienski
M. Movassaghi*, M. Tjandra, J. Qi
Massachusetts Institute of Technology, Cambridge, USA
Total Synthesis of (-)-Himandrine
J. Am. Chem. Soc.  2009,  131:  9648-9650  
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
20. November 2009 (online)


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 (JK).