English
 
User Manual Privacy Policy Disclaimer Contact us
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

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

MPS-Authors
/persons/resource/persons58824

Micoine,  Kevin
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58380

Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

External Ressource
No external resources are shared
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)

[279]SI.pdf
(Supplementary material), 17MB

Citation

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.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-8DF9-1
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.