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Issue 6, 1988
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Stereocontrolled synthesis of the brassinolide side-chain: formal synthesis of brassinolide

Tetsuji Kametani,  Masaharu Kigawa,  Masayoshi Tsubuki  and  Toshio Honda 

Abstract

The stereoselective introduction of the brassinolide side-chain, having a (20S,22R,23R,24S)-22,23-diol functionality, was examined. The catalytic reduction of (20S,22R,24Z)-6β-methoxy-23-oxo-3α,5-cyclo-5α-stigmast-24(28)-eno-29,22-lactone (11), derived from the 20-carbaldehyde (7) and 3-isopropyl-2-lithiofuran in three steps, afforded (20S,22R,23R,24S)-22-hydroxy-6β-methoxy-3α,5-cyclo-5α-stigmastano-29,23-lactone (14), an important intermediate for the stereoselective synthesis of brassinolide.

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Article type: Paper
DOI: 10.1039/P19880001503
Citation: J. Chem. Soc., Perkin Trans. 1, 1988,0, 1503-1507
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    Stereocontrolled synthesis of the brassinolide side-chain: formal synthesis of brassinolide

    T. Kametani, M. Kigawa, M. Tsubuki and T. Honda, J. Chem. Soc., Perkin Trans. 1, 1988, 0, 1503
    DOI: 10.1039/P19880001503

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