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Synfacts 2021; 17(09): 0968
DOI: 10.1055/s-0040-1720837
Synthesis of Natural Products and Potential Drugs

Synthesis of (±)-Paeoniflorigenin

Contributor(s):
Erick M. Carreira
,
Moritz J. Classen
Corey EJ, *, Wu Y.-J. Harvard University, Cambridge, USA
Total Synthesis of (±)-Paeoniflorigenin and Paeoniflorin.

J. Am. Chem. Soc. 1993;
115: 8871-8872
DOI: 10.1021/ja00072a063.
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Key words

(±)-paeoniflorigenin - Paeonia lactiflora - Prilezhaev reaction - Reformatsky-type cyclization

Significance

In 1993, Corey and Wu reported the synthesis of (±)-paeoniflorigenin, a natural product from the roots of paenia lactiflora, which are widely used in traditional Chinese medicine. The approach relies on oxidative annulation of dihydro-m-cresol ether A and SmI2-induced, Reformatsky-type cyclization from an α-chloro nitrile.


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Comment

The synthesis commenced with annulation of A and B to give γ-lactone C. Chlorination followed by Prilezhaev epoxidation yields E. Cyclization is achieved by treating lactol F with an excess of TMS-triflate. Exposure of H to SmI2 leads to formation of the carbon skeleton of paeniflorigenin. Protection of the secondary alcohol followed by ­reduction of the nitrile gives K. Benzoylation and global deprotection completed the total synthesis of (±)-paeniflorigenin in 13 steps from A.


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Publication History

Article published online:
18 August 2021

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