128041-98-5Relevant articles and documents
Support Studies for Formulating the Nine Contiguous Chiral Centres of Streptovaricin A Ansa Chain
Mootoo, David R.,Fraser-Reid, Bert
, p. 739 - 746 (2007/10/02)
The tripyranoside (1b), which had been previously prepared as a key intermediate for the synthesis of the streptovaricin A ansa chain, lacks synthons for the C-24-CO2Me and C-28 tertiary alcohol of the antibiotic .The 'upper' acetal ring of (1b) has been cleaved selectively, an exocyclic methylene is develeoped at C-6, and a hydroboration sequence has been used to install an axial hydroxymethyl group as the synthon for the CO2Me group.In order to provide a self-consistent means of structure verification, both epimers of the C-10 tertiary alcohol have been prepared by utilizing empirically determined strategies for acyclic stereoselection.