Synthesis of secasterone and further epimeric 2,3- epoxybrassinosteroids

Abstract

As part of a programme directed towards the synthesis of new native brassinosteroids and biologically active analogues we synthesized (22R,23R,24S)-2α,3α-epoxy-22,23-dihydroxy-24-methyl-5α-cholestan-6-one and (22R,23R,24S)-2β,3β-epoxy-22,23-dihydroxy-24-methyl-5α-cholestan-6-one (secasterone) as well as both the corresponding 2,3-epoxides of the (24R)-series. In addition, the isomeric 3-dehydro-24-epi-teasterone has been prepared. The bioactivity of the new compounds is discussed.