Total Synthesis of (+)-Myriocin and (-)-Sphingofungin E from Aldohexoses Using Overman Rearrangement as the Key Reaction.

…, K Ando, K Inomiya, H Sato, M Iida, N Chida

Index: Oishi, Takeshi; Ando, Koji; Inomiya, Kenjin; Sato, Hideyuki; Iida, Masatoshi; Chida, Noritaka Bulletin of the Chemical Society of Japan, 2002 , vol. 75, # 9 p. 1927 - 1947

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Citation Number: 56

Abstract

Total synthesis starting from aldohexoses of naturally occurring α-substituted α-amino acids,(+)-myriocin (1) and (−)-sphingofungin E (2), is described. Overman rearrangement of allylic trichloroacetimidate 6E derived from D-mannose effectively generated the tetrasubstituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized moiety 3 of myriocin stereoselectively. Sulfone-mediated coupling reaction ...