55730-86-4Relevant academic research and scientific papers
Epoxides in Synthesis. Synthesis of the Novel 2,6-Dioxabicyclooctane Units in the Citreoviridinols and the Aurovertins
Forbes, Judith E.,Bowden, Martin C.,Pattenden, Gerald
, p. 1967 - 1973 (2007/10/02)
The 2,6-dioxabicyclooctane ring system, viz. systems 24 and 34, present in citreoviridinol and the aurovertins, have been produced in a stereoselective manner by treatment of the corresponding 4-hydroxytetrahydrofuran epoxides 22 and 33, respectively, with toluene-p-sulphonic acid.A number of related epoxy alcohol cyclisations leading to isomeric dioxabicyclooctanes are reported.These studies have led to a greater understanding of the biosynthetic pathway to the citreoviridinols and the aurovertins, and a greater appreciation of the role of epoxide intermediates in the biosynthesis apparatus.
