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Lingzhiol November 26.pdf (1022.6 kB)
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8-Step Enantiodivergent Synthesis of (+)- and (-)-Lingzhiol

preprint
revised on 02.12.2019 and posted on 02.12.2019 by Paul S. Riehl, Alistair D. Richardson, Tatsuhiro Sakamoto, Corinna Schindler

An 8-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.

Funding

David and Lucile Packard Foundation, Alfred P. Sloan Foundation, Camille and Henry Dreyfus Foundation, NIGMS R01-GM118644

History

Email Address of Submitting Author

corinnas@umich.edu

Institution

University of Michigan

Country

United States

ORCID For Submitting Author

0000-0003-4968-8013

Declaration of Conflict of Interest

No conflict of interest

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