First diastereoselective total synthesis of bicyclic styryl lactone: (1R,5R,7R)-7-((E)-styryl)-2,6-dioxabicyclo[3.3.1]nonan-3-one
[Display omitted] A concise and facile diastereoselective first total synthesis of bicyclic styryl lactone 1 is described in nine steps. This biologically active bicyclic styryl lactone was obtained in 8% overall yield from cinnamaldehyde 2 and (R)-3-hydroxyhex-5-enoic acid 3. Jacobsen resolution, P...
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Published in | Results in Chemistry Vol. 5; p. 100717 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Elsevier B.V
01.01.2023
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | [Display omitted]
A concise and facile diastereoselective first total synthesis of bicyclic styryl lactone 1 is described in nine steps. This biologically active bicyclic styryl lactone was obtained in 8% overall yield from cinnamaldehyde 2 and (R)-3-hydroxyhex-5-enoic acid 3. Jacobsen resolution, Pinnick oxidation and Prins cyclisation reactions are the key steps involved in the synthesis. |
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ISSN: | 2211-7156 2211-7156 |
DOI: | 10.1016/j.rechem.2022.100717 |