Two Total Syntheses of Trigoxyphins K and L.

ABSTRACT: Two total syntheses are presented for trigoxyphins K and L, tricyclic terpenoids from Trigonostemon xyphophylloides. The first proceeds via electrophlic cyclization in A/C-ring substrates to close the B ring at C4-C5 and then ¹O₂-mediated hydroxybutenolide formation to trigoxyphin L, with Luche reduction leading to trigoxyphin K. The second route develops from tetralone ring expansion to a B/C-ring intermediate that, by one-step O-demethylation-lactonization-isomerization, affords trigoxyphin K and then trigoxyphin L following enolate oxygenation.

SUBMITTER: Li S 

PROVIDER: S-EPMC10594648 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature