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DOI: 10.1055/s-0042-1753241
Total Synthesis of (–)-Peyssonnoside A
Catalysis-Enabled 13-Step Total Synthesis of (–)-Peyssonnoside A.
J. Am. Chem. Soc. 2022;
144: 19700-19703
DOI: 10.1021/jacs.2c09919.
Key words
(–)-peyssonnoside A - diterpene glycoside - marine natural product - antimicrobial - dearomative cyclization - HAT-initiated cyclization - Wittig reaction - Mukaiyama hydration![](https://www.thieme-connect.de/media/synfacts/202302/i_c008_s1_10-1055_s-0042-1753241.gif)
Significance
Dai and co-workers present a concise synthesis of (–)-peyssonnoside A, a sulfated diterpene glycoside which was isolated in 2019 from the red alga Peyssonnelia sp. (–)-Peyssonnoside A stands out through its sterically encumbered, pentasubstituted cyclopropane ring which represents a key synthetic challenge.
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Comment
Enantioselective conjugate addition to enone A and subsequent enolate trapping with propargyl bromide D furnished ketone E. Palladium-catalyzed hydroarylation and functional group interconversion to phenol H set the stage for dearomative cyclization to dienone J. HAT-initiated cyclization secured the encumbered cyclopropane K and paved the way to (–)-peyssonnoside A.
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Publication History
Article published online:
17 January 2023
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