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  Total Synthesis of Belizentrin Methyl Ester: Report on a Likely Conquest

Anderl, F., Größl, S., Wirtz, C., & Fürstner, A. (2018). Total Synthesis of Belizentrin Methyl Ester: Report on a Likely Conquest. Angewandte Chemie International Edition, 57(33), 10712-10717. doi:10.1002/anie.201805125.

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[377]SI.pdf (Supplementary material), 17MB
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 Creators:
Anderl, Felix1, Author              
Größl, Sylvester1, Author              
Wirtz, Conny2, Author              
Fürstner, Alois1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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Free keywords: cross coupling; Kocienski olefination; macrocyclization; marine natural products; polyenes
 Abstract: The assigned structure of the dinoflagellate-derived toxin belizentrin was prepared by total synthesis in form of the corresponding methyl ester for stability reasons. The successful route features an unusual solution for the preparation of a recalcitrant ylid on a C-glycosidic segment; moreover, it involves an asymmetric hetero-Diels/Alder reaction en route to the tertiary hemiacetal substructure, a Negishi cross coupling of two elaborate building blocks, and a macrocyclization based on an intramolecular aminolysis of a spirolactone. A modified Kocienski olefination ultimately allowed the polyol side chain to be attached to the macrocycle, although this transformation faced the exceptional base-sensitivity of this polyunsaturated target compound.

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Language(s): eng - English
 Dates: 2018-05-022018-06-012018-08-13
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201805125
 Degree: -

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Title: Angewandte Chemie International Edition
  Other : Angew. Chem., Int. Ed.
  Other : Angew. Chem. Int. Ed.
  Other : Angewandte Chemie, International Edition
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 57 (33) Sequence Number: - Start / End Page: 10712 - 10717 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851