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

Full Text: HTML

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 ...

Related Articles:

Arene-catalysed lithiation of triflates and triflamides under barbier-type conditions: An indirect transformation of alcohols and amines into organolithium compounds

[Alonso, Emma; Ramon, Diego J.; Yus, Miguel Tetrahedron, 1996 , vol. 52, # 45 p. 14341 - 14348]

Anomalous Densities of 1-n-Alkyl-cyclohexanols

[Williams; Edwards Journal of the American Chemical Society, 1947 , vol. 69, p. 336]

SN2 displacements and reductive coupling of ketones with olefins in N, N-diethylacetamide and N-ethylpyrrolidone

[Sowinski,A.F.; Whitesides,G.M. Journal of Organic Chemistry, 1979 , vol. 44, # 14 p. 2369 - 2376]

More Articles...