jo5008948_si_001.cif (26.99 kB)

Total Synthesis of (−)-Dihydrosporothriolide Utilizing an Indium-Mediated Reformatsky–Claisen Rearrangement

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posted on 20.06.2014, 00:00 by Jun Ishihara, Hiroaki Tsuru, Susumi Hatakeyama
The asymmetric synthesis of (−)-dihydrosporothriolide (1), a biologically active bis-γ-butyrolactone, is described, that proceeds through a d-proline-catalyzed asymmetric aminooxylation, indium-mediated Reformatsky–Claisen rearrangement of an α,α-dibromoacetate derivative, and diastereoselective dihydroxylation. The route requires no protective group manipulation and allows the concise seven-step synthesis of 1 from n-octanal.