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  Asymmetric Synthesis of the Fully Functional Macrolide Core of Salicylihalamide:  Remote Control of Olefin Geometry during RCM

Fürstner, A., Thiel, O. R., & Blanda, G. (2000). Asymmetric Synthesis of the Fully Functional Macrolide Core of Salicylihalamide:  Remote Control of Olefin Geometry during RCM. Organic Letters, 2(23), 3731-3734. doi:10.1021/ol006646d.

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[125]SI.pdf (Supplementary material), 99KB
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 Creators:
Fürstner, Alois1, Author              
Thiel, Oliver R.1, Author              
Blanda, Gaetano1, Author
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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 Abstract: A catalysis-based approach to the core region 24 of the antitumor agents salicylihalamides A and B is reported. Key steps are two asymmetric hydrogenations of β-keto esters 13 and 16 catalyzed by [(R)-BINAP·RuCl2]2·NEt3 and an RCM-based macrocyclization effected by the NHC-containing ruthenium carbene 21. The stereochemical outcome of the latter reaction is controlled by remote substituents on the phenolic OH group of the cyclization precursor 23.

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Language(s): eng - English
 Dates: 2000-09-252000-10-272000-11-16
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ol006646d
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Title: Organic Letters
  Other : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: 4 Volume / Issue: 2 (23) Sequence Number: - Start / End Page: 3731 - 3734 Identifier: ISSN: 1523-7060
CoNE: https://pure.mpg.de/cone/journals/resource/954925626338