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26-Norbrassinolide, identified as a metabolite of brassinolide in cultured cells of the liverwort, Marchantia polymorpha, as well as 26-norcastasterone and 26-nor-6-deoxocastasterone were synthesized. Synthesis of these new brassinosteroids was conducted by employing the orthoester Claisen rearrangement and asymmetric dihydroxylation as key reactions. The modified rice lamina inclination test indicated...
As a reference compound library for the investigation of biosynthesis of brassinosteroids, focused on a pathway from campesterol (1) to campestanol (2), 6-oxy functionalized campest-4-en-3-ones as well as campest-5-en-3-one (7) and campestane-3,6-dione were prepared from 1. Oxidation of 1 with pyridinium chlorochromate buffered by calcium carbonate gave 5-en-3-one (7) in 76% yield. Treatment of 7...
With a view to attaining more precise information on the biological activity of 2,3,5-tri-epi-brassinolide analogs, 2,3,5-tri-epi-brassinolide was prepared from 2,3-di-epi-brassinolide by direct epimerization at C-5. Biological activity of 2,3,5-tri-epi-brassinolide in the rice lamina inclination test was nil even at 1<space>μg/plant by the single application technique, while with co-application...
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