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Synfacts 2017; 13(08): 0779
DOI: 10.1055/s-0036-1590672
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (–)-Flueggenine C

Authors

    Contributor(s):

  • Erick M. Carreira

  • Robert J. Gillespie

Jeon S. Han S. * Korea Advanced Institute of Science and Technology, Daejeon and Institute for Basic Science, Daejeon, Republic of Korea
An Accelerated Intermolecular Rauhut–Currier Reaction Enables the Total Synthesis of (–)-Flueggenine C.

J. Am. Chem. Soc. 2017;
139: 6302-6305
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Further Information

Publication History

Publication Date:
18 July 2017 (online)

 
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Key words

securinega alkaloids - (–)-flueggenine C - Rauhut–Currier reaction - dimerization - Horner–Wadsworth–Emmons reaction

Significance

Jeon and Han report the first total synthesis of the dimeric securinega alkaloid (–)-flueggenine C. The key dimerization step is enabled by a bio-inspired Rauhut–Currier reaction accelerated by the presence of an internal nucleophile. This reaction is pertinent in the biosynthesis of dimeric and oligomeric securinega alkaloids.


 

Comment

After efficiently synthesizing intermediate C in seven steps and 14% overall yield, the pivotal Rauhut–Currier dimerization and subsequent acetylation provided D in 74% yield. HWE olefination of F afforded unsaturated lactone G. The final ring closure was facilitated by SN2 displacement of a mesylate culminating at the natural product.


 

 


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