Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using overman rearrangement as the key reaction

Takeshi Oishi, Koji Ando, Kenjin Inomiya, Hideyuki Sato, Masatoshi Iida, Noritaka Chida

研究成果: Article査読

55 被引用数 (Scopus)

抄録

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 of the allyl bromide 3 with C12 hydrophobic part 4 successfully constructed the carbon framework possessing E-olefin 28. Removal of the sulfone and protecting groups completed the chiral and stereoselective total synthesis of (+)-myriocin (1). A similar transformation starting from D-glucose also accomplished the total synthesis of (-)-sphingofungin E (2).

本文言語English
ページ(範囲)1927-1947
ページ数21
ジャーナルBulletin of the Chemical Society of Japan
75
9
DOI
出版ステータスPublished - 2002 9

ASJC Scopus subject areas

  • 化学 (全般)

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