Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision**
Publication date
2021-08-02
Authors
Holzheimer, M.
Sinninghe Damste, Jaap S.
Schouten, S.
Havenith, R.W.A.
Cunha, A.V.
Minnaard, A.J.
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Abstract
Crenarchaeol is a glycerol dialkyl glycerol tetraether lipid produced exclusively in Archaea of the phylum Thaumarchaeota. This membrane-spanning lipid is undoubtedly the structurally most sophisticated of all known archaeal lipids and an iconic molecule in organic geochemistry. The 66-membered macrocycle possesses a unique chemical structure featuring 22 mostly remote stereocenters, and a cyclohexane ring connected by a single bond to a cyclopentane ring. Herein we report the first total synthesis of the proposed structure of crenarchaeol. Comparison with natural crenarchaeol allowed us to propose a revised structure of crenarchaeol, wherein one of the 22 stereocenters is inverted.
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Holzheimer, M, Sinninghe Damsté, J S, Schouten, S, Havenith, R W A, Cunha, A V & Minnaard, A J 2021, 'Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision**', Angewandte Chemie - International Edition, vol. 60, no. 32, pp. 17504-17513. https://doi.org/10.1002/anie.202105384