Publication: Bioinspired asymmetric synthesis of (-)-gymnothelignan v
Issued Date
2018-04-06
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ISSN
15206904
00223263
00223263
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2-s2.0-85045127239
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Organic Chemistry. Vol.83, No.7 (2018), 4173-4179
Suggested Citation
Darunee Soorukram, Manat Pohmakotr, Chutima Kuhakarn, Vichai Reutrakul Bioinspired asymmetric synthesis of (-)-gymnothelignan v. Journal of Organic Chemistry. Vol.83, No.7 (2018), 4173-4179. doi:10.1021/acs.joc.8b00164 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/45500
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Title
Bioinspired asymmetric synthesis of (-)-gymnothelignan v
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Abstract
© 2018 American Chemical Society. A bioinspired asymmetric total synthesis of a structurally unique subtype of lignan, namely, (-)-gymnothelignan V, was achieved. The key synthetic sequences involved reduction of the eupomatilone skeleton leading to (-)-gymnothelignan J followed by the formation of the corresponding oxocarbenium ion and stereoselective intramolecular Friedel-Crafts reaction. Our synthetic approach provides the information to support the plausible biosynthetic pathway of this structurally unusual lignan. On a similar basis, other structurally related natural and non-natural gymnothelignans including (-)-gymnothelignan D, 6,9-bis-epi-gymnothelignan V, and 5-epi-gymnothelignans D and J were readily prepared.