99972-97-1Relevant academic research and scientific papers
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.
Unexpected cis-selectivity in (Sylvestre) Julia Olefinations with Bu 3Sn-containing allyl benzothiazolyl sulfones: Stereoselective synthesis of 1,3-butadienyl- and 1,3,5-hexatrienylstannanes
Sorg, Achim,Brückner, Reinhard
, p. 289 - 293 (2007/10/03)
Bu3Sn-substituted benzothiazolyl sulfones 1c, 1d, and 1f were subjected to Julia olefmation reactions with a variety of aldehydes. cis-Selectivities up to 97:3 were obtained by using KHMDS as base in THF.
