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Synthetic Studies toward the C14–C29 Fragment of Mirabalin

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Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231, ESPCI Paris/CNRS/PSL Research University, 10 rue Vauquelin 75231 Cedex 05 Paris, France
PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France
Cite this: Org. Lett. 2016, 18, 18, 4534–4537
Publication Date (Web):September 7, 2016
https://doi.org/10.1021/acs.orglett.6b02162
Copyright © 2016 American Chemical Society

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    Abstract

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    A convergent synthesis of one isomer of the C14–C29 fragment of mirabalin is disclosed. The key steps include a Marshall allenylation, a Mukaiyama aldol reaction and a Crimmins aldolization, which allow the control of 10 out of 25 stereogenic centers present in the molecule.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.6b02162.

    • Experimental procedures and full spectroscopic data for all new compounds (PDF)

    • X-ray data for compound cis-19′ (CIF)

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