Stereoselective synthesis of the C9-C19 fragment of lyngbyaloside B and C via ether transfer.
A stereoselective synthesis of the C9-C19 fragment of lyngbyaloside B and C highlighted, by an extension of our ether transfer methodology, enables the formation of tertiary ethers. 2-Naphthylmethyl ethers have been shown to proceed efficiently through ether transfer with high stereoselectivity and are easily deprotected by DDQ oxidation. Variation of the workup conditions results in the stereoselective formation of syn-1,3-diol mono- or diethers.
Department of Chemistry and Biochemistry and the Mike and Josie Harper Cancer Research Institute, University of Notre Dame, 251 Niewland Science Hall, Notre Dame, Indiana 46556, USA.
Eric
E
Stefan
Richard E
RE
Taylor
D004987:Ethers / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D004987:Ethers; D018942:Macrolides; C473445:lyngbyaloside B; C576098:lyngbyaloside C