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Synthesis 2018; 50(22): 4359-4368
DOI: 10.1055/s-0037-1610437
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© Georg Thieme Verlag Stuttgart · New York

Short Enantioselective Formal Synthesis of (–)-Platencin

Christian Defieber
a   The 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 
a   The 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
b   Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607, USA   Email: stoltz@caltech.edu
,
Gennadii A. Grabovyi
b   Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607, USA   Email: stoltz@caltech.edu
,
Brian M. Stoltz*
a   The 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
› Author AffiliationsWe thank the NIH-NIGMS (R01 GM080269), DAAD (postdoctoral fellowship to C.D.), Eli Lilly (predoctoral fellowship to J.T.M.), Amgen, Bristol-Myers Squibb, Merck Research Laboratories, Abbott Laboratories, Boehringer-Ingelheim, and Caltech for generous funding. We also thank the UIC Department of Chemistry (startup funds to J.T.M.) and the National Science Foundation (CAREER Award 1654490 to J.T.M.).
Further Information

Publication History

Received: 03 May 2018

Accepted after revision: 29 May 2018

Publication Date:
23 July 2018 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610437.
  • Supporting Information
 

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