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Total synthesis of the alleged structure of crenarchaeol enables structure revision
Holzheimer, M.; Sinninghe Damste, J.S.; Schouten, S.; Havenith, R.W.A.; Minnaard, A.J. (2021). Total synthesis of the alleged structure of crenarchaeol enables structure revision. Angew. Chem. 133(32): 17645-17654. https://doi.org/10.1002/ange.202105384
In: Angewandte Chemie. Wiley: Weinheim. ISSN 1433-7851; e-ISSN 1521-3773, more
Peer reviewed article  
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  • Holzheimer, M.
  • Sinninghe Damste, J.S., more
  • Schouten, S., more
  • Havenith, R.W.A.
  • Minnaard, A.J.
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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