1229345-53-2Relevant academic research and scientific papers
Total synthesis of auripyrone b using a non-Aldol Aldol-Cuprate opening process
Jung, Michael E.,Chaumontet, Manon,Salehi-Rad, Ramin
supporting information; experimental part, p. 2872 - 2875 (2010/08/21)
(Figure presented) A non-aldol aldol-cuprate opening generates the polypropionate 11 from the epoxy ether 14 in eight steps as a single diastereomer. A highly stereoselective aldol reaction of 8 with 9 gives the aldol product 7 in high yield and excellent diastereoselectivity, due to double stereodifferentiation. This compound was used for an efficient synthesis of the natural product auripyrone B 2 in only 20 steps and 8% overall yield from 14 using a late-stage spiroketalization onto a stable hemiketal as the final key step.
