An Approach towards the Synthesis of the Spiroimine Fragment of 13-Desmethylspirolide C and Gymnodimine A

Alexandre Guthertz; Jonathan Lusseau; Valérie Desvergnes; Stéphane Massip; Yannick Landais

doi:10.1002/chem.201804972

An Approach towards the Synthesis of the Spiroimine Fragment of 13-Desmethylspirolide C and Gymnodimine A

Chemistry. 2019 Jan 28;25(6):1553-1560. doi: 10.1002/chem.201804972. Epub 2019 Jan 2.

Authors

Alexandre Guthertz¹, Jonathan Lusseau¹, Valérie Desvergnes¹, Stéphane Massip², Yannick Landais¹

Affiliations

¹ Institute of Molecular Sciences (ISM), UMR-CNRS 5255, University of Bordeaux, 351 Cours de la libération, 33405 Talence cedex, France.
² European Institute of Chemistry and Biology (IECB), University of Bordeaux, 2 Rue Robert Escarpit, 33600, Pessac, France.

PMID: 30358921
DOI: 10.1002/chem.201804972

Abstract

A general access to the spiroimine skeleton of gymnodimine and spirolides is described, relying on the construction of the cyclohexene fragment using an enantiocontrolled Diels-Alder reaction, the installation of the all-carbon quaternary stereocenter through a stereocontrolled alkylation or aldolisation and the elaboration of the lateral chains at C7 and C22 using Wittig-Horner olefinations. The spiroimine core of gymnodimine is made available through a 16-step linear sequence in a 21 % overall yield.

Keywords: Diels-Alder reaction; asymmetric synthesis; natural products; quaternary stereocenters; spiroimine.

Abstract

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