99972-97-1Relevant articles and documents
Concise total synthesis of the potent translation and cell migration inhibitor lactimidomycin
Micoine, Kevin,Fuerstner, Alois
supporting information; experimental part, p. 14064 - 14066 (2011/01/04)
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 [(Ph 3SiO)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.
