Isolation and relay synthesis of 11α-hydroperoxy diacetyl hederagenin, a novel triterpenoid derivative from Serjania triquetra (Sapindaceae). Biogenetic implications

Article abstract of DOI:10.1016/S0040-4020(01)89663-0

Stigmasterol, oleanolic acid, morolic acid, hederagenin, and 11α-hydroperoxy-hederagenin were isolated and characterized as the sapogenins present in the aerial parts of the medicinal plant Serjania triquetra (Sapindaceae). The structure of the novel triterpenoid derivative, 11α-hydroperoxy-diacetyl hederagenin, considered as a key biogenetic and chemical intermediate, was confirmed by relay synthesis from diacetyl hederagenin, via bromo-lactonization, dehydrobromination, and oxidation with H₂O₂. Biogenetic relationships are briefly described.