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  The Formosalides: Structure Determination by Total Synthesis

Schulthoff, S., Hamilton, J. Y., Heinrich, M., Kwon, Y., Wirtz, C., & Fürstner, A. (2021). The Formosalides: Structure Determination by Total Synthesis. Angewandte Chemie International Edition, 60(1), 446-454. doi:10.1002/anie.202011472.

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 Creators:
Schulthoff, Saskia1, Author              
Hamilton, James Y.1, Author              
Heinrich, Marc1, Author              
Kwon, Yonghoon1, 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: alkyne metathesis; natural products; platinum; structure elucidation; total synthesis
 Abstract: Total synthesis allowed the constitution of the cytotoxic marine macrolides of the formosalide family to be confirmed and their previously unknown stereostructure to be assigned with confidence. The underlying blueprint was inherently modular to ensure that each conceivable isomer could be reached. This flexibility derived from the use of strictly catalyst controlled transformations to set the stereocenters, except for the anomeric position, which is under thermodynamic control; as an extra safety measure, all stereogenic centers were set prior to ring closure to preclude any interference of the conformation adopted by the macrolactone rings of the different diastereomers. Late‐stage macrocyclization by ring‐closing alkyne metathesis was followed by a platinum‐catalyzed transannular 6‐exo‐dig hydroalkoxylation/ketalization to craft the polycyclic frame. The side chain featuring a very labile unsaturation pattern was finally attached to the core by Stille coupling.

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Language(s): eng - English
 Dates: 2020-08-212020-09-112020-09-182021-01-04
 Publication Status: Published in print
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202011472
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 60 (1) Sequence Number: - Start / End Page: 446 - 454 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851