Total Synthesis of the Alleged Structure of Crenarchaeol enables Structure Revision

Mira Holzheimer, Jaap S Sinninghe Damsté, Stefan Schouten, Remco W A Havenith, Ana V Cunha, Adriaan J Minnaard*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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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.

Original languageEnglish
Pages (from-to)17504-17513
JournalAngewandte Chemie (International ed. in English)
Volume60
Issue number32
Early online date11-Jun-2021
DOIs
Publication statusPublished - 2-Aug-2021

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