Stereoselective synthesis and moulting activity of integristerone A and analogues
摘要:
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-5 alpha-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 1 beta-hydroxyl group resulted in a decrease in activity. As expected, the 1,2-di-epi-5 alpha-analogue was inactive in this assay. (c) 2006 Elsevier Ltd. All rights reserved.
Stereoselective synthesis and moulting activity of integristerone A and analogues
摘要:
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-5 alpha-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 1 beta-hydroxyl group resulted in a decrease in activity. As expected, the 1,2-di-epi-5 alpha-analogue was inactive in this assay. (c) 2006 Elsevier Ltd. All rights reserved.