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Updated: Jan 1, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Eight-Step Enantiodivergent Synthesis of (+)- and (-)-Lingzhiol
Paul S Riehl1, Alistair D Richardson1, Tatsuhiro Sakamoto1
1Department of Chemistry , University of Michigan , Willard Henry Dow Laboratory, 930 North University Avenue , Ann Arbor , Michigan 48109 , United States.
Abstract:
An eight-step enantioselective synthesis of lingzhiol is described herein. The sense of an asymmetric Michael reaction is reversed by the choice of metal source, enabling facile access to both enantiomers. A spontaneous semipinacol ring contraction enables mild construction of the lingzhiol core, and radical-mediated benzylic oxidation proceeds in the presence of an unprotected secondary alcohol. This represents the shortest enantioselective synthesis of lingzhiol to date and the only enantiodivergent approach to both enantiomers of this meroterpenoid natural product.
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