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Studies on the Synthesis of Steroidal Plant-Growth Hormones; XVIII. A Convenient Route to 26,27-Bisnorbrassinolide
10
Citations
0
References
1990
Year
Bioorganic ChemistryEngineeringOrganic ChemistryChemistryDiversity Oriented SynthesisBiosynthesisOverall YieldConvenient RouteNatural Product BiosynthesisSteroid MetabolismDiversity-oriented SynthesisSteroidal Plant-growth HormonesPharmacologyNatural Product SynthesisPhytochemistryEnantioselective SynthesisBiomolecular EngineeringBiologyNatural SciencesReductive EliminationSynthetic ChemistrySix-step Sequence
(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.