Abstract

Integristerone A, a rare ecdysteroid of plant origin, has been synthesized from 20-hydroxyecdysone with 2-deoxy-1,2-didehydro-20-hydroxyecdysone as the key intermediate, followed by stereoselective asymmetric dihydroxylation. The analogues 1,2-di- epi-integristerone A and 1,2-di- epi-5α-integristerone A have also been synthesized. Integristerone A exhibited approximately 9-fold lower moulting activity than the parent 20-hydroxyecdysone in the Musca domestica bioassay, indicating that the presence of a 1β-hydroxyl group resulted in a decrease in activity. As expected, the 1,2-di- epi-5α-analogue was inactive in this assay.

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