Tandem conjugate addition-elimination for the diastereoselective synthesis of 4E-alkenyl syn-1,3-diols.
We have developed a tandem conjugate addition-elimination sequence for the diastereoselective synthesis of protected allylic syn-1,3-diols, starting from vinyl sulfones. The sulfonyl group was then reduced with sodium amalgam to furnish the E-olefin as the major isomer. This method was applied to the synthesis of a trisubstituted alkene modeling the C21-C25 fragment of Dolabelide C.
Rotulo-Sims
Delphine
D
Laboratoire de Synthèse Organique, UMR CNRS 7652, Ecole Polytechnique, DCSO, F-91128 Palaiseau, France.
Prunet
Joëlle
J
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry
D000438:Alcohols; D000475:Alkenes; D004224:Diterpenes; D018942:Macrolides; D013450:Sulfones; C524147:dolabelide C; C009873:divinyl sulfone