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Synfacts 2022; 18(12): 1279
DOI: 10.1055/s-0042-1753059
DOI: 10.1055/s-0042-1753059
Synthesis of Natural Products
Total Synthesis of (±)-Rameswaralide
Authors
Truax NJ,
Ayinde S,
Liu JO,
Romo D.
*
Baylor University, Waco, USA
Total Synthesis of Rameswaralide Utilizing a Pharmacophore-Directed Retrosynthetic Strategy.
J. Am. Chem. Soc. 2022;
144: 18575-18585
DOI: 10.1021/jacs.2c08245
Total Synthesis of Rameswaralide Utilizing a Pharmacophore-Directed Retrosynthetic Strategy.
J. Am. Chem. Soc. 2022;
144: 18575-18585
DOI: 10.1021/jacs.2c08245
Key words
(±)-rameswaralide - cembranoid diterpene - Diels–Alder reaction - Simmons–Smith cyclopropanation - Stille cross-coupling - Wacker–Tsuji oxidation - Michael addition - Julia–Kocienski olefination
Significance
Romo and co-workers report the first total synthesis of (±)-rameswaralide. The natural product is active against the A549 lung cancer cell line. The synthesis enabled study of the natural product and intermediates in assays for cyctotoxicity.
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Comment
The seven-membered ring in rameswaralide is accessed by cyclopropanation of enol ether G and subsequent ring expansion to the dibromide I. The precursor N for the Michael addition is accessed in a convergent manner by cross coupling J and K.
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Publication History
Article published online:
17 November 2022
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