L-トレイトール誘導体を共通キラル素子として活用する天然物合成

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This article reviews our own work on the recent development of the methodology for chiral preparation of nitrogen-containing natural products including alkaloids, antibiotics etc. utilizing 4-<I>O</I>-benzyl-2, 3-<I>O</I>-bis (methoxymethyl) -L-threitol (1), readily available from L-tartaric acid, as a common chiral synthon. The strategy for the natural product synthesis is based on regulating the stereochemical course of nucleophilic addition to the α, β-bis [(methoxymethyl) oxy] carbonyl and imino systems with highly selective diastereofacial differentiation in chelation or nonchelation processes, which are predictable. Also, this approach has allowed us to demonstrate the marked versatility of 1 as a synthetically very flexible chiral building block.
社団法人有機合成化学協会の論文