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Unified approach to the sesquiterpenoids,lauranes and cyclolauranes: Total synthesis of (±)-isolaurene |
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| Authors: | Sovan Niyogi Arindam Khatua Vishnumaya Bisai |
| Institution: | 1. Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal 462 066, Madhya Pradesh, India;2. Department of Chemistry, Indian Institute of Science Education and Research Berhampur, Berhampur 760 010, Odisha, India |
| Abstract: | A general approach to the total synthesis of sesquiterpene, isolaurene (1a) and cyclolaurene (2a) is featured from commercially available 3-methyl cyclopenten-2-one. The strategy includes a Stork-Danheiser sequence concomitant with a Ni(II)-catalyzed conjugate addition of methyl group onto 3-aryl 2-methyl cyclopenten-2-one to afford the advanced intermediate 11. A methyllithium addition onto compound 11 with an eventual dehydration completed the total synthesis of isolaurene (1a) in 5 steps (58.3% overall yields). |
| Keywords: | Corresponding author at: Department of Chemistry Indian Institute of Science Education and Research Bhopal Bhauri Bhopal 462 066 Madhya Pradesh India Laurane sesquiterpenoids Isolaurene Stork-Danheiser sequence Vinylogous esters |
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