Total synthesis of the formamicin aglycon, formamicinone.
[structure: see text] The total synthesis of formamicinone (2), the aglycone of formamicin (1), has been accomplished via the late-stage Suzuki cross-coupling of fragments 5 and 6, the macrolactonization of seco ester 14, and the Mukaiyama aldol reaction of aldehyde 3 and methyl ketone 4. An efficient and highly stereoselective second generation synthesis of vinyl iodide 6 is also described.
Savall
Brad M
BM
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
Blanchard
Nicolas
N
Roush
William R
WR
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D018942:Macrolides; D015394:Molecular Structure
D000900:Anti-Bacterial Agents; D018942:Macrolides; C111293:formamicin