Journal
TETRAHEDRON
Volume 76, Issue 27, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131297
Keywords
Clavigerin; Total synthesis; Antifeedant; Claisen rearrangement; Optical resolution
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Funding
- JSPS KAKENHI [23102010]
- Grants-in-Aid for Scientific Research [23102010] Funding Source: KAKEN
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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 1S,3S,6S,8S,9R. (C) 2020 Elsevier Ltd. All rights reserved.
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