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Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision **
Author(s) -
Holzheimer Mira,
Sinninghe Damsté Jaap S.,
Schouten Stefan,
Havenith Remco W. A.,
Cunha Ana V.,
Minnaard Adriaan J.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202105384
Subject(s) - stereocenter , ring (chemistry) , cyclopentane , cyclohexane , chemistry , stereochemistry , biochemistry , catalysis , organic chemistry , enantioselective synthesis
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.