Abstract
Stachysterone C was synthesized from 20-hydroxyecdysone (20-ECD). Sharpless asymmetric dihydroxylation of this rare ecdysteroid using osmium tetroxide and a chiral ligand afforded 24- epi-abutasterone, another rare ecdysteroid, and its C-24 epimer, abutasterone. High diastereomeric excess of the former ecdysteroid was obtained when the chiral ligands dihydroquinidine 1,4-phthalazinediyl diether and dihydroquinidine 2,5-diphenyl-4,6-pyrimidinediyl diether were employed. The two C-24 epimeric ecdysteroids exhibited similar moulting hormone activity in the Musca bioassay. However, they were significantly less active than 20-ECD.
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