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- W4244367035 abstract "Several reported syntheses of brassinolide, (22R,23R,24S)- 2α,3α,22,23-tetrahydroxy-24-methyl-B-homo-7-oxa-5α-cholestan-6-one, involve a C-22 aldehyde derived from stigmasterol, which is used for construction of the sidechain with chiral centers at C-22, C-23 and C-24. In our synthesis, (20 S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carboxaldehyde was reacted with the anion of 2,3-dimethylbutenolide at -78 °C to give a lactone which was readily converted to the desired sidechain. Functionalization of the steroid nucleus completed the synthesis. We have investigated an alternative approach starting from 22,23-bisnor-5-cholenic acid-3β-ol acetate, in which functionalization of the nucleus is first carried out leading to the intermediate 6-ethylenedioxy-2α,3α-isopropylidenedioxy-bisnor-5α-cholanal. The aldehyde can be used in aldol condensations with the lithium salt of 2,3-dimethylbutenolide or of 3-isopropylbutenolide, giving analogs of brassinolide with the natural 22R,23R stereochemistry." @default.
- W4244367035 created "2022-05-12" @default.
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- W4244367035 date "1991-11-04" @default.
- W4244367035 modified "2023-09-25" @default.
- W4244367035 title "Synthesis of Brassinolide" @default.
- W4244367035 doi "https://doi.org/10.1021/bk-1991-0474.ch004" @default.
- W4244367035 hasPublicationYear "1991" @default.
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