1. Total synthesis of both enantiomers of clavigerins B and C.
- Author
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Kakimoto, Nozomu, Ogura, Yusuke, Watanabe, Hidenori, and Takikawa, Hirosato
- Subjects
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ENANTIOMERS , *OPTICAL rotation , *SESQUITERPENES , *CLAISEN rearrangement , *OPTICAL resolution , *SKELETON - Abstract
The first total synthesis of both enantiomers of clavigerins B and C, insect antifeedant sesquiterpenes isolated from New Zealand liverwort Lepidolaena clavigera , has been achieved. The synthesis features Ireland-Claisen rearrangement for construction of bicyclo[3.1.1]heptene skeleton. By comparison of the optical rotations of both enantiomers with those of natural clavigerins, the absolute configurations of natural clavigerins B and C were unambiguously determined to be 1 S ,3 S ,6 S ,8 S ,9 R. Image 1 • The first synthesis of both enantiomers of clavigerins B and C was achieved. • Clavigerins are bergamotane sesquiterpenes exhibiting insect antifeedant activity. • Ireland-Claisen rearrangement was featured as the key step to construct bicyclo[3.1.1]heptene skeleton. • The absolute configurations of natural clavigerins B and C were unambiguously determined. [ABSTRACT FROM AUTHOR]
- Published
- 2020
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