Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach |
| |
| Institution: | 1. Université de Bourgogne, LEAD/CNRS, UMR5022, Pôle AAFE, 11 Esplanade Erasme, 21000 Dijon, France;2. CNRS, UMR5292, INSERM U1028, Lyon Neuroscience Research Center, Auditory Cognition and Psychoacoustics Team, Université of Lyon I, Lyon, France;3. Laboratoire de Psychologie et Neurocognition, CNRS UMR5105, Université Grenoble Alpes, Bâtiment Sciences de l''Homme et Mathématiques, BP47, 38040 Grenoble Cedex 9, France;1. School of Veterinary Medicine, Kitasato University, Towada, Aomori 034-8628, Japan;2. Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan;3. Obihiro University of Agriculture & Veterinary Medicine, 2-11 Inadacho-Nishi, Obihiro, Hokkaido 080-8555, Japan;4. Faculty of Environmental Earth Science, Hokkaido University, North 10, West 5, Kita-ku, Sapporo 060-0810, Japan;6. Southeast Environmental Research Center, and Department of Chemistry and Biochemistry, Florida International University, 3000 NE 151 Street, North Miami 33181, USA;5. Sarawak State Tropical Peat Research Laboratory, Jalan Badruddin, 93000 Kuching, Sarawak, Malaysia |
| |
| Abstract: | 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. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
