Short Enantioselective Formal Synthesis of (–)-Platencin

Christian Defieber; Justin T. Mohr; Gennadii A. Grabovyi; Brian M. Stoltz

doi:10.1055/s-0037-1610437

Synthesis, Table of Contents

Synthesis 2018; 50(22): 4359-4368
DOI: 10.1055/s-0037-1610437

paper

Short Enantioselective Formal Synthesis of (–)-Platencin

Christian Defieber

^aThe Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering California Institute of Technology, 1200 E California Blvd. MC 101-20, Pasadena, CA 91125, USA

,

Justin T. Mohr

^aThe Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering California Institute of Technology, 1200 E California Blvd. MC 101-20, Pasadena, CA 91125, USA

^bDepartment of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607, USA Email: stoltz@caltech.edu

,

Gennadii A. Grabovyi

^bDepartment of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607, USA Email: stoltz@caltech.edu

,

Brian M. Stoltz*

^aThe Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering California Institute of Technology, 1200 E California Blvd. MC 101-20, Pasadena, CA 91125, USA

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Abstract

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Dedicated to Prof. Dr. Scott E. Denmark on the occasion of his 65th birthday.

Abstract

A short enantioselective formal synthesis of the antibiotic natural product platencin is reported. Key steps in the synthesis include enantioselective decarboxylation alkylation, aldehyde/olefin radical cyclization, and regioselective aldol cyclization.

Key words

formal synthesis - palladium - enantioselective reactions - enantioconvergent synthesis - alkylation

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References

References
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