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Synthesis 1989; 1989(6): 426-427
DOI: 10.1055/s-1989-27273
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Studies on Steroidal Plant-Growth :Regulators: A New Synthesis of Brassinosteroids

Wei-Shan Zhou* , Yi-Pine Zhou, Biao Jiang
  • *Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Lu, Shanghai, People's Republic of China
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Publication Date:
17 September 2002 (online)

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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.