Total syntheses of (-)-lycoricidine,(+)-lycoricidine, and (+)-narciclasine via 6-exo cyclizations of substituted vinyl radicals with oxime ethers

GE Keck, TT Wager, JFD Rodriquez

Index: Keck, Gary E.; Wager, Travis T.; Duarte Rodriquez, J. Felix Journal of the American Chemical Society, 1999 , vol. 121, # 22 p. 5176 - 5190

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Citation Number: 80

Abstract

The development of an approach to the total synthesis of the title alkaloids is described. The approach utilizes as the key strategic element a stereoselective 6-exo radical cyclization of a vinyl radical to an O-benzyloxime radical acceptor group. The vinyl radical was itself generated by regioselective addition of phenylthiyl radical to a disubstituted alkyne. The regiochemical issues of such additions, which result in different outcomes with tri-n- ...