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Synfacts 2015; 11(9): 0897
DOI: 10.1055/s-0034-1378755
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (–)-Jiadifenolide

Contributor(s):
Erick M. Carreira
,
Matthias Westphal
Lu H.-H, Martinez MD, Shenvi RA * The Scripps Research Institute, La Jolla, USA
An Eight-Step Gram-Scale Synthesis of (–)-Jiadifenolide.

Nat. Chem. 2015;
7: 604-607
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Publication History

Publication Date:
18 August 2015 (online)

 
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Key words

(–)-jiadifenolide - stereoselective coupling - neurotrophic terpenes

Significance

Jiadifenolide is one of a number of secondary metabolites with neurotrophic activity isolated from the Illicium genus. The authors present a short route towards this natural product relying on a diastereoselective coupling of two buten­olides. The strategy might allow for the synthesis of structurally related neurotrophic natural products.


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Comment

Chiral bicycle D was prepared from (+)-citronellal via a short dehydration–ozonolysis–hetero-Pauson–Khand sequence. The lithium dienolate derived from D was diastereoselectively coupled with building block F to give the entire carbon skeleton G upon treatment with excess LDA and Ti(Oi-Pr)4. Four more steps allowed the isolation of considerable amounts of jiadifenolide.


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