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Stereoselective synthesis of (2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide starting from 2,5-anhydro-d-mannitol |
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| Authors: | Shunya Takahashi Narihito Ogawa Tadashi Nakata |
| Institution: | a RIKEN (The Institute of Physical and Chemical Research), Wako-shi, 351-0198 Saitama, Japan b Graduate School of Environmental Earth Science, Hokkaido University, Kita-ku 060-0810 Sapporo, Japan c Department of Chemistry, Faculty of Science, Tokyo University of Science, 1-3, Kagurazaka, Shinjuku-Ku, 162-8601 Tokyo, Japan |
| Abstract: | A novel approach to natural β-hydroxy-γ-lactone 2 from 2,5-anhydro-d-mannitol (1) is described. The key reactions in this synthesis include stereoselective methylation of aldehyde 3 with lithium dimethylcuprate, an intramolecular radical cyclization of seleno carbonate 11 and an intermolecular cross-metathesis of 3-allyl-4-hydroxy-γ-lactone 16 with 1-tridecene. |
| Keywords: | 2 d-mannitol" target="_blank">5-Anhydro-d-mannitol Intramolecular radical cyclization Intermolecular cross-metathesis |
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