Darunee SoorukramManat PohmakotrChutima KuhakarnVichai ReutrakulMahidol University2019-08-232019-08-232018-04-06Journal of Organic Chemistry. Vol.83, No.7 (2018), 4173-417915206904002232632-s2.0-85045127239https://repository.li.mahidol.ac.th/handle/20.500.14594/45500© 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.Mahidol UniversityChemistryArticleSCOPUS10.1021/acs.joc.8b00164