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Enantioselective Total Synthesis of (+)‐Neostenine |
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| Authors: | Yasuaki Nakayama Yuichiro Maeda Masayuki Kotatsu Ruriko Sekiya Masato Ichiki Dr. Takaaki Sato Prof. Dr. Noritaka Chida |
| Affiliation: | Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan |
| Abstract: | A chirality transfer approach using acyclic polyol intermediates for the synthesis of (+)‐neostenine ( 1 ) has been developed. The sequential Overman/Claisen rearrangement of an allylic 1,2‐diol was especially useful, installing two contiguous stereocenters with complete diastereoselectivity in a one‐pot sequence. The SmI2‐mediated cyclization and the subsequent chemoselective reduction of a lactam moiety accomplished the first enantioselective total synthesis of (+)‐neostenine ( 1 ). |
| Keywords: | alkaloid allylic compound diol sigmatropic rearrangement total synthesis |