764-58-9Relevant articles and documents
Applications of crotonyldiisopinocampheylboranes in synthesis: Total synthesis of restrictinol
Barrett, Anthony G. M.,Bennett, Adrian J.,Menzer, Stefan,Smith, Marie L.,White, Andrew J. P.,Williams, David J.
, p. 162 - 171 (2007/10/03)
The total synthesis of restrictinol, the hydrolysis product of the antifungal natural product restricticin, starting from commercially available methyl (S)-(+)-3-hydroxy-2-methylpropionate is described. Key stages in the strategy involved (i) the use of Brown's allylboration chemistry to construct an acyclic intermediate bearing three of the four stereogenic centers of the natural product, (ii) formation of a C-glycosidic vinyl iodide, and (iii) introduction of the triene side chain via a Suzuki coupling reaction.
DIASTEREOSELECTIVE SYNTHESIS OF (E)-1-TRIMETHYLSILYL-3-EN-1-YNES BY PALLADIUM-CATALYZED CROSS-COUPLING REACTION BETWEEN TRIMETHYLSILYLETHYNYLZINC CHLORIDE AND STEREOISOMERIC MIXTURES OF 1-BROMO-1-ALKENES
Andreini, Bianca Patrizia,Carpita, Adriano,Rossi, Renzo
, p. 5533 - 5534 (2007/10/02)
In the stereospecific palladium-catalyzed cross-coupling reaction of trimethylsilylethynylzinc chloride, (E)-1-bromo-1-alkenes react preferentially in the presence of the corresponding (Z)-stereoisomers.