A novel rearrangement of eudesmanolide enol ester epoxide: facile 1-step construction of the salvialane sesquiterpene skeleton |
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| Institution: | 1. The Key Laboratory of Beam Technology and Material Modification of the Ministry of Education, Beijing Normal University, Beijing 100875, China;2. College of Nuclear Science and Technology, Beijing Normal University, Beijing 100875, China |
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| Abstract: | A novel carbon–carbon rearrangement for the eudesmanolide sesquiterpene enol ester epoxide in the presence of a catalytic amount of Lewis acids (3–10 mol%) or an excess of NaOMe is disclosed. This reaction was developed to give a facile, one-step procedure for the construction of naturally occurring and bioactive salvialane sesquiterpenes. The reaction conditions were investigated extensively and a possible reaction mechanism is also discussed. |
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