950905-47-2Relevant academic research and scientific papers
Total synthesis of efomycine M
Barth, Roland,Mulzer, Johann
, p. 5791 - 5794 (2007)
(Chemical Equation Presented) Two-directional synthesis: Key steps in the first total synthesis of the anti-inflammatory agent efomycine M (1) are a two-directional C11-C12 chain elongation and an early-stage dimerization reaction. The central stereopentad is synthesized by a highly stereoselective sequence consisting of an onti-aldol reaction and a diastereoselective reduction.
Two-directional total synthesis of efomycine M and formal total synthesis of elaiolide
Barth, Roland,Mulzer, Johann
, p. 4718 - 4735 (2008/09/21)
The anti-inflammatory agent efomycine M (1) has been synthesized from macrodilactone 38 and vinyliodide 42 by a two-directional total synthesis in 17 steps over the longest linear sequence with an overall yield of 7%. The C2-symmetric macrodiolide 38 has been prepared by Yamaguchi macrolactonization of seco-acid 26. The central stereopentad of 1 was obtained by a highly efficient anti-aldol reaction followed by a diastereoselective ketone reduction. Additionally, we have completed a formal total synthesis of elaiolide (3) by converting macrodiolide 37 into Paterson's methylketone 13.
