Literature DB >> 11772113

Total synthesis of sphingofungin E from D-glucose.

Takeshi Oishi1, Koji Ando, Kenjin Inomiya, Hideyuki Sato, Masatoshi Iida, Noritaka Chida.   

Abstract

[reaction: see text] Total synthesis of sphingofungin E (1) is described. Overman rearrangement of an allylic trichloroacetimidate derived from diacetone-D-glucose generated tetra-substituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized part in sphingofungin E (4) stereoselectively. Coupling reaction of 4 with the C(12) hydrophobic part, followed by further manipulation, completed the total synthesis.

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Year:  2002        PMID： 11772113     DOI： 10.1021/ol0171620

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  4 in total

1.  Total Synthesis of (-)-Bastimolide A: A Showcase for Type I Anion Relay Chemistry.

Authors:  Joshua B Cox; Alex A Kellum; Yiwen Zhang; Bo Li; Amos B Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-24       Impact factor: 16.823

2.  A formal [3,3]-sigmatropic rearrangement route to quaternary alpha-vinyl amino acids: use of allylic N-PMP trifluoroacetimidates.

Authors:  David B Berkowitz; Bin Wu; Huijie Li
Journal:  Org Lett       Date:  2006-03-02       Impact factor: 6.005

3.  A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C.

Authors:  Luka Raguž; Chia-Chi Peng; Marcel Kaiser; Helmar Görls; Christine Beemelmanns
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-07       Impact factor: 16.823

4.  Microwave accelerated aza-Claisen rearrangement.

Authors:  Eva Gajdosíková; Miroslava Martinková; Jozef Gonda; Patrik Conka
Journal:  Molecules       Date:  2008-11-14       Impact factor: 4.411
  4 in total

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