Revision and Confirmation of the Regiochemistry of Isoxazoles Derived from Methyl Oleanonate and Lanost-8-en-3-one. Synthesis of a New Lanostane Triterpenoid with a Cyano-enone Functionality in Ring A

Abstract

It was previously reported that methyl oleanonate (5) and lanost-8-en-3-one (10) give predominantly [3,2-c]isoxazoles. On the contrary, we have confirmed that both compounds 5 and 10 do not give [3,2-c]isoxazoles but rather afford regioselectively [2,3-d]isoxazoles in good yields. Consequently, a new lanostane triterpenoid with a cyano-enone functionality in ring A was synthesized in two steps from the corresponding [2,3-d]isoxazole, which is interesting from the perspective of biological activity because lanosterol is the biogenetic precursor of steroids.