Total synthesis of (-)-dihydrosporothriolide utilizing an indium-mediated Reformatsky-Claisen rearrangement.
作者： Jun Ishihara , Hiroaki Tsuru , Susumi Hatakeyama
DOI: 10.1021/JO5008948
关键词: Derivative (chemistry) 、 Molecule 、 Chemistry 、 Claisen rearrangement 、 4-Butyrolactone 、 Total synthesis 、 Combinatorial chemistry 、 Stereoisomerism 、 Enantioselective synthesis 、 Dihydroxylation 、 Stereochemistry
摘要: The asymmetric synthesis of (-)-dihydrosporothriolide (1), a biologically active bis-γ-butyrolactone, is described, that proceeds through D-proline-catalyzed aminooxylation, indium-mediated Reformatsky-Claisen rearrangement an α,α-dibromoacetate derivative, and diastereoselective dihydroxylation. route requires no protective group manipulation allows the concise seven-step 1 from n-octanal.
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