Investigation of acetyl migrations in furanosides

• O. P. Chevallier and
• M. E. Migaud

Beilstein J. Org. Chem. 2006, 2, No. 14, doi:10.1186/1860-5397-2-14

• acetyl moieties. Such direct transesterification is intermolecular and while it has been observed in nucleoside-phosphoramidite and glycoside chemistry,[20][21][22][23] this alkoxide-promoted intermolecular acetyl migration process has been overlooked in furanosides. The isolated quantities of 1c and 1d

Stereoselective α-fluoroamide and α-fluoro- γ-lactone synthesis by an asymmetric zwitterionic aza-Claisen rearrangement

• Kenny Tenza,
• Julian S. Northen,
• David O'Hagan and
• Alexandra M. Z. Slawin

Beilstein J. Org. Chem. 2005, 1, No. 13, doi:10.1186/1860-5397-1-13

• intermediate in the synthesis of the anti-HIV nucleoside β-FddA1 6. [17][18] Results and discussion In order to undertake the appropriate zwitterionic aza-Claisen rearrangement reactions an efficient method for the production of the α-fluoro acid chloride substrates was required. A number of routes to 2

• iodolactonisation to generate α-fluoro-γ-butyrolactones, with good diastereoselectivities (~80–100% de). These molecules are useful intermediates for further derivatisation in the area of nucleoside analogue synthesis and the method is complementary to asymmetric electrophilic fluorination strategies for the