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  Concise Total Synthesis of the Potent Translation and Cell Migration Inhibitor Lactimidomycin

Micoine, K., & Fürstner, A. (2010). Concise Total Synthesis of the Potent Translation and Cell Migration Inhibitor Lactimidomycin. Journal of the American Chemical Society, 132(40), 14064-14066. doi:10.1021/ja107141p.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-000F-8DF9-1 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0028-1AC8-E
Genre: Journal Article

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[279]SI.pdf (Supplementary material), 17MB
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 Creators:
Micoine, Kevin1, Author           
Fürstner, Alois1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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 Abstract: An efficient total synthesis of the antiproliferative macrolide and cell migration inhibitor lactimidomycin (3) is reported, which relies on the performance of ring closing alkyne metathesis (RCAM). The strained 12-membered 1,3-enyne 21 as the key intermediate was forged with the aid of [(Ph3SiO)3Mo≡CPh]·OEt2 (27) as the most effective member of a new generation of powerful alkyne metathesis catalysts. 21 was elaborated to the target by a ruthenium catalyzed trans-hydrosilylation/proto-desilylation sequence and a highly diastereoselective Mukaiyama aldol reaction controlled by oxazaborolidinone 29 as strategic operations.

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Language(s): eng - English
 Dates: 2010-08-092010-09-102010-10-13
 Publication Status: Issued
 Pages: 3
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 541649
DOI: 10.1021/ja107141p
ISI: 000282660100039
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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 132 (40) Sequence Number: - Start / End Page: 14064 - 14066 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870