A highly efficient, selective, and general method for the synthesis of conjugated (all-E)-oligoenes of the (CH=CH)n type via iterative hydrozirconation-palladium-catalyzed cross-coupling.
[reaction: see text] A linear iterative method for the construction of (all-E)-oligoenes of the (CH=CH)n type via hydrozirconation-palladium-catalyzed cross-coupling with (E)-1-bromo-4-trimethylsilyl-1-buten-3-yne is described. This method promises to provide an efficient, selective, and general route to oligoene macrolide antibiotics and other related natural products.
Zeng
Fanxing
F
Herbert C. Brown Laboratories of Chemistry, Purdue University, West Lafayette, Indiana 47907-1393, USA.
Negishi Ei
Ei-ichi
E
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D001685:Biological Factors / Q000138:chemical synthesis; D002384:Catalysis; D018942:Macrolides; D010165:Palladium / Q000737:chemistry; D011090:Polyenes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry
D000900:Anti-Bacterial Agents; D001685:Biological Factors; D018942:Macrolides; D011090:Polyenes; D010165:Palladium; D015040:Zirconium