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Synfacts 2025; 21(03): 221
DOI: 10.1055/a-2518-3175
DOI: 10.1055/a-2518-3175
Synthesis of Natural Products
Total Synthesis of (–)-Scabrolide B
Simmons EJ,
Ryffel DB,
Lopez DA,
Boyko YD,
Sarlah D *.
Rice University, Houston and University of Illinois at Urbana−Champaign, Urbana, USA
Total Syntheses of Scabrolide B, Ineleganolide, and Related Norcembranoids.
J. Am. Chem. Soc. 2025;
147: 130-135
DOI: 10.1021/jacs.4c16629
Total Syntheses of Scabrolide B, Ineleganolide, and Related Norcembranoids.
J. Am. Chem. Soc. 2025;
147: 130-135
DOI: 10.1021/jacs.4c16629
Keywords
(–)-scabrolide B - nickel-mediated [3+2] annulation - Wittig homologation - Mukaiyama–Michael addition - Mukaiyama aldol reaction
Significance
Sarlah and co-workers report the total synthesis of (–)-scabrolide B. The authors chose a convergent approach to the 5 /7 /6-norcembranoid-type natural product by disconnecting the central seven-membered ring into fragment H and norcarvone (I).
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Comment
Starting from building block C, developed by the group of Sarlah in 2023, lactone H was synthesized in three steps. A sequence of Mukaiyama−Michael/aldol reactions gave access to the full carbon skeleton of the natural product in an efficient manner.
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Publication History
Article published online:
25 February 2025
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