Tetrahedron
Tetrahedron
5 years ago

Synthesis of 1,10-seco-triterpenoids by the Beckmann fragmentation from allobetulin

Synthesis of 1,10-seco-triterpenoids by the Beckmann fragmentation from allobetulin
A new convenient route to synthesize 1,10-seco-triterpenoids from allobetulin was demonstrated. Stereoisomerism of starting oleanane 1-oximes was determined by X-ray crystallography and additionally confirmed by the structure of the obtained Beckmann rearrangement products. Absolute configuration of chiral centers of 1,10-secotriterpenoids was found to be identical to that of stereocenters in respective precursors. Antiviral activity of 1,10-seco-derivatives was studied against herpes simplex virus type I.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017309808

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