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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Bibliographic Details
Published inResults in Chemistry Vol. 5; p. 100717
Main Authors Biradar, Dhanraj O., Mane, Yogesh D., Narsaiah, A.V., Subba Reddy, B.V.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.01.2023
Elsevier
Subjects
Bicyclic styryl lactone
Cryptocaryolone
Prins cyclisation
Pyranopyrone
Bicyclic styryl lactone
Cryptocaryolone
Prins cyclisation
Pyranopyrone
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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.
ISSN:2211-7156
2211-7156
DOI:10.1016/j.rechem.2022.100717