880145-53-9Relevant academic research and scientific papers
Formal enantioselective synthesis of (+)-compactin
Robichaud, Joel,Tremblay, Francois
, p. 597 - 600 (2007/10/03)
The challenging structural features and important biological activity of (+)-compactin (1) explain the substantial synthetic interest that it has generated. We report a novel enantioselective approach to the advanced intermediate 2a, which constitutes a formal synthesis of (+)-1. The sequence utilizes MacMillan's organocatalytic Mukaiyama-Michael reaction, which stereoselectively adds the silyloxyfuran 6 to α,β-unsaturated aldehyde 7. The chirality generated in this reaction guides the formation of the other three consecutive stereocenters found in 2a.
