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Synthesis 1990; 1990(11): 1073-1075
DOI: 10.1055/s-1990-27098
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Studies on the Synthesis of Steroidal Plant-Growth Hormones; XVIII. A Convenient Route to 26,27-Bisnorbrassinolide

Wei-Shan Zhou* , Hui-Qiang Zhou, G. Roussi, Zhi-Qin Wang
  • *Shanghai Institute of Organic Chemistry, Academia Sinica, 345 Lingling Lu, Shanghai 200032, Peoples' Republic of China
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Publication Date:
17 September 2002 (online)

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(22R,23R)-22,23-Isopropylidenedioxy-6-oxo-24-nor-5α-cholest-2-ene (10), a precursor of 26,27-bisnorbrassinolide (2), is synthesized from the α, β-unsaturated (22R,23R)-γ-lactone 4 by a six-step sequence: hydrogenation, reduction, oxidation, decarbonylation, and reductive elimination. The overall yield is 29% from 4 to 10.

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