Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c5sc04144a Click here for additional data file.

نویسندگان

  • Ryan J. Beattie
  • Thomas W. Hornsby
  • Gemma Craig
  • M. Carmen Galan
  • Christine L. Willis
چکیده

A de novo approach for the rapid construction of orthogonally protected Land D-deoxysugars and analogues is described. A novel and robust silicon-acetal undergoes Prins cyclisations with a series of homoallylic alcohols in high yield and excellent stereocontrol. Modified Tamao–Fleming oxidation of the resulting silyltetrahydropyrans gives direct access to deoxyglycoside analogues and the approach was showcased in the synthesis of protected L-oliose, a component of the anticancer agent aclacinomycin A.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations.

A de novo approach for the rapid construction of orthogonally protected l- and d-deoxysugars and analogues is described. A novel and robust silicon-acetal undergoes Prins cyclisations with a series of homoallylic alcohols in high yield and excellent stereocontrol. Modified Tamao-Fleming oxidation of the resulting silyltetrahydropyrans gives direct access to deoxyglycoside analogues and the appr...

متن کامل

First total synthesis of concavine† †Electronic supplementary information (ESI) available. CCDC 1523963. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc05627j Click here for additional data file. Click here for additional data file.

The synthesis of the unusual alkaloid concavine, isolated from Clitocybe concava (Basidiomycetae), has been accomplished. The synthetic route features regioand stereoselective manipulation of polycyclic imide intermediates via enolate substitution and Grignard addition, along with a key bridge-forming step involving a new method for sulfenylative radical cyclisation. The NMR data for synthetic ...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:

دوره 7  شماره 

صفحات  -

تاریخ انتشار 2016