Studies on Steroidal Plant-Growth :Regulators: A New Synthesis of Brassinosteroids
- 1 June 1989
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1989 (06) , 426-427
- https://doi.org/10.1055/s-1989-27273
Abstract
Two brassinosteroids (stereoisomers of brassinolide), (22R,23R,24R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one (2) and (22S,23S,24R)-2α,3α,22, 23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one (3), were synthesized from ergosterol in eight steps in ca. 30% overall yield. The key step is the highly regioselective formation of the 7-oxalactone ring by oxidation of an enol silyl ether with 3-chloroperoxybenzoic acid.Keywords
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