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Synfacts 2023; 19(08): 0741
DOI: 10.1055/s-0042-1752823
DOI: 10.1055/s-0042-1752823
Synthesis of Natural Products
Synthesis of (–)-Retigeranic Acid A
Sun D,
Chen R,
Tang D,
Xia Q,
Zhao Y,
Liu C.-H,
Ding H.
*
Zhejiang University, Hangzhou, P. R. of China
Total Synthesis of (–)-Retigeranic Acid A: A Reductive Skeletal Rearrangement Strategy.
J. Am. Chem. Soc. 2023;
145: 11927-11932
DOI: 10.1021/jacs.3c03178
Total Synthesis of (–)-Retigeranic Acid A: A Reductive Skeletal Rearrangement Strategy.
J. Am. Chem. Soc. 2023;
145: 11927-11932
DOI: 10.1021/jacs.3c03178
Key words
(–)-retigeranic acid A - Henry condensation - Nef reaction - Wittig olefination - Robinson annulation - Meinwald rearrangement - cycloaddition and pinacol rearrangement - reductive rearrangement - Wolff ring contraction
Significance
Ding and co-workers present a total synthesis of (–)-retigeranic acid A, isolated in 1965 from linchens of the Lobaria retigera. The pentacyclic carbon framework contains a unique trans-hydrindane-fused angular triquinane.
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Comment
The trans-hydrindane is assembled from keto aldehyde A featuring a Henry condensation and Nef reaction under oxidative conditions. Homologation and addition of aryl bromide G led to benzylic alcohol H, that underwent cycloaddition and pinacol rearrangement. From triketone J, the carbon skeleton of (–)-retigeranic acid A was accessed via reductive rearrangement and Wolff ring contraction.
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Publication History
Article published online:
14 July 2023
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