Abstract
We report on the synthesis of the brassinosteroid analogs (22R,23R)-3β,7β,22,23-tetrahydroxy-stigmast-5-ene ( 13), (22R,23R)-3β,7α,22,23-tetrahydroxy-stigmast-5-ene ( 15), and (22R,23R)-3β,22,23-trihydroxy-stigmast-5,7-diene ( 18) by means of the osmium-catalyzed asymmetric dihydroxylation of intermediate 1, available from stigmasterol. This reaction sequence produced the expected (22S,23S)- and (22R,23R)-triols 6 and 7 as well as the 22,23-diketo derivatives 2 and 3. The phytohormone activity of the new brassinosteroid analogs is discussed.
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