A Unified Approach for the Total Synthesis of cyclo‐Archaeol, iso‐Caldarchaeol, Caldarchaeol, and Mycoketide

Ir‐catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established 13C‐NMR method to determine the enantioselectivity of each methyl‐branched stereoc...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2021-08, Vol.60 (32), p.17497-17503
Main Authors: Andringa, Ruben L. H., Kok, Niels A. W., Driessen, Arnold J. M., Minnaard, Adriaan J.
Format: Article
Language:English
Subjects:
Archaea
asymmetric hydrogenation
Enantiomers
lipids
membrane spanning
metathesis
NMR
Nuclear magnetic resonance
Stereoselectivity
Terpenes
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Summary:Ir‐catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established 13C‐NMR method to determine the enantioselectivity of each methyl‐branched stereocenter. It is shown that this analysis is fit for purpose and the combination allows the synthesis of the title compounds with a significant increase in efficiency. Cyclo‐archaeol, iso‐caldarchaeol, caldarchaeol, and mycoketide are prepared by employing asymmetric hydrogenation to generate the multiple stereocenters.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202104759