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Synfacts 2023; 19(08): 0741
DOI: 10.1055/s-0042-1752823
Synthesis of Natural Products

Synthesis of (–)-Retigeranic Acid A

Contributor(s):
Erick M. Carreira
,
Sander Folkerts
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
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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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