Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach
- Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach
- 윤호종; 조경선; 심태보
- (+)-lentiginosine; 천연물 전합성
- Issue Date
- Tetrahedron, asymmetry
- VOL 25, NO 6-7, 497-502
- The synthesis of the indolizidine alkaloid, (+)-lentiginosine, is described. A key feature of the preparative route is the efficient and stereoselective construction of a dihydroxylated pyrrolidine via Sharpless asymmetric dihydroxylation of an aziridine-enoate, which was prepared from commercially available 1-(S)-α-methylbenzylaziridine-2-methanol. In addition, a regioselective aziridine-to-pyrrolidinone ring expansion process followed by a Wittig olefination was employed to construct a late stage pyrrolidine intermediate that was transformed into (+)-lentiginosine.
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