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  Catalysis-Based Total Synthesis of Putative Mandelalide A

Willwacher, J., & Fürstner, A. (2014). Catalysis-Based Total Synthesis of Putative Mandelalide A. Angewandte Chemie International Edition, 53(16), 4217-4221. doi:10.1002/anie.201400605.

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anie_201400605_sm_miscellaneous_information-2.pdf (Supplementary material), 10MB
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anie_201400605_sm_miscellaneous_information-2.pdf
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Supporting information
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Copyright Date:
2014
Copyright Info:
Wiley-VCH 69451 Weinheim, Germany
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 Creators:
Willwacher, Jens1, Author           
Fürstner, Alois1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: alkyne metathesis; molybdenum; natural products; structure elucidation; total synthesis
 Abstract: A concise synthesis of the putative structure assigned to the highly cytotoxic marine macrolide mandelalide A (1) is disclosed. Specifically, an iridium-catalyzed two-directional Krische allylation and a cobalt-catalyzed carbonylative epoxide opening served as convenient entry points for the preparation of the major building blocks. The final stages feature the first implementation of terminal-acetylene metathesis into natural product synthesis, which is remarkable as this class of substrates was beyond reach until very recently; key to success was the use of the highly selective molybdenum alkylidyne complex 42 as the catalyst. Although the constitution and stereochemistry of the synthetic samples are unambiguous, the spectra of 1 as well as of 11-epi-1 deviate from those of the natural product, which implies a subtle but deep-seated error in the original structure assignment.

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Language(s): eng - English
 Dates: 2014-01-202014-03-122014-04-14
 Publication Status: Issued
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201400605
 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: 5 Volume / Issue: 53 (16) Sequence Number: - Start / End Page: 4217 - 4221 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851