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 [(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.
Micoine, Kevin,Fuerstner, Alois
supporting information; experimental part
p. 14064 - 14066
(2011/01/04)
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
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.
Sorg, Achim,Brückner, Reinhard
p. 289 - 293
(2007/10/03)
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