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

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...

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Veröffentlicht in:	Journal of the American Chemical Society 2010-10, Vol.132 (40), p.14064-14066
Hauptverfasser:	Micoine, Kevin, Fürstner, Alois
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Cell Movement - drug effects Humans Macrolides - chemical synthesis Macrolides - pharmacology Piperidones - chemical synthesis Piperidones - pharmacology Protein Biosynthesis - drug effects
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container_title	Journal of the American Chemical Society
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creator	Micoine, Kevin Fürstner, Alois
description	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.
doi_str_mv	10.1021/ja107141p
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subjects	Animals Cell Movement - drug effects Humans Macrolides - chemical synthesis Macrolides - pharmacology Piperidones - chemical synthesis Piperidones - pharmacology Protein Biosynthesis - drug effects
title	Concise Total Synthesis of the Potent Translation and Cell Migration Inhibitor Lactimidomycin
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