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J Am Chem Soc. 2009 Jul 22;131(28):9648-50. doi: 10.1021/ja903790y.

Total synthesis of (-)-himandrine.

Author information

1
Massachusetts Institute of Technology, Department of Chemistry, Cambridge, Massachusetts 02139, USA. movassag@mit.edu

Abstract

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.

PMID:
19555115
PMCID:
PMC2752835
DOI:
10.1021/ja903790y
[Indexed for MEDLINE]
Free PMC Article

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