162189-53-9Relevant articles and documents
Total synthesis of soraphen A(1α)
Abel, Stephan,Faber, Dominik,Hueter, Ottmar,Giese, Bernd
, p. 188 - 197 (2007/10/03)
The convergent synthesis of macrolide soraphen A(1α) is described starting from glucose (western part) and mannose (eastern part). Mannose was converted into a 2-deoxyribohexopyranoside that could be methylated and reduced stereoselectively. Chain elongation at C-6 was carried out by stereoselective addition of a magnesium acctylide. The two fragments (western and eastern) were assembled by a Julia olefination followed by macrolactonization. The introduction of the methyl group at C-2 of norsoraphen occurred stereoselectively for thermodynamic reasons.