Enantiospecific total synthesis of (-)-bakkenolide III and formal total synthesis of (-)-bakkenolides B, C, H, L, V, and X |
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Authors: | Jiang Chiao-Hua Bhattacharyya Annyt Sha Chin-Kang |
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Institution: | Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan, ROC. |
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Abstract: | A concise enantiospecific synthesis of (-)-bakkenolide III was accomplished from (S)-(+)-carvone. The key step involved radical cyclization of an iodoketone intermediate which afforded the cis-hydrindanone skeleton. Further synthetic transformations generated bakkenolide III, which also constitutes the formal total synthesis of (-)-bakkenolides, B, C, H, L, V, and X. |
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