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  Metathesis at an Implausible Site: A Formal Total Synthesis of Rhizoxin D

Karier, P., Ungeheuer, F., Ahlers, A., Anderl, F., Wille, C., & Fürstner, A. (2019). Metathesis at an Implausible Site: A Formal Total Synthesis of Rhizoxin D. Angewandte Chemie International Edition, 58(1), 248-253. doi:10.1002/anie.201812096.

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anie201812096-sup-0001-misc_information-1.pdf (Supplementary material), 6MB
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anie201812096-sup-0001-misc_information-1.pdf
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 Creators:
Karier, Pol1, Author              
Ungeheuer, Felix1, Author              
Ahlers, Andreas1, Author              
Anderl, Felix1, Author              
Wille, Christian1, Author              
Fürstner, Alois1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: 1,3-dienes, alkynes, macrocycles, natural products, trans-hydrostannation
 Abstract: The new approach to the anticancer agent rhizoxin D described herein does not cohere with the conventional logic of metathesis, according to which macrocycles are best closed at a disubstituted olefinic site; rather, the trisubstituted C11−C12 alkene flanked by an allylic ‐OH group served as the pivot point for synthesis. This motif was attained in good yield and excellent selectivity by a sequence of alkyne metathesis, trans‐hydrostannation and cross coupling. Because the exact same substructure is prominently featured in numerous other natural products, the underpinning strategy, though unusual, might bear more general relevance.

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Language(s): eng - English
 Dates: 2018-10-222018-11-152019-01-02
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201812096
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Title: Angewandte Chemie International Edition
  Other : Angewandte Chemie, International Edition
  Other : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 58 (1) Sequence Number: - Start / End Page: 248 - 253 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851