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

Authors :
Andringa, Ruben L. H.
de Kok, Niels A. W.
Driessen, Arnold J. M.
Minnaard, Adriaan J.
Chemical Biology 2
Molecular Microbiology
Source :
Angewandte Chemie (International Ed. in English), Angewandte Chemie (International ed. in English), 60(32), 17497-17503. WILEY-V C H VERLAG GMBH
Publication Year :
2021
Publisher :
Wiley, 2021.

Abstract

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.<br />Cyclo‐archaeol, iso‐caldarchaeol, caldarchaeol, and mycoketide are prepared by employing asymmetric hydrogenation to generate the multiple stereocenters.

Details

ISSN :
15213773 and 14337851
Volume :
60
Database :
OpenAIRE
Journal :
Angewandte Chemie International Edition
Accession number :
edsair.doi.dedup.....1195bd8ec740d5227f42791349e7258a
Full Text :
https://doi.org/10.1002/anie.202104759