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Stereoselective synthesis of the brassinolide side chain; novel syntheses of brassinolide and related compounds

✍ Scribed by Zhou Wei-shan; Jiang Biao; Pan Xin-fu

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
813 KB
Volume
46
Category
Article
ISSN
0040-4020

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✦ Synopsis

A stereoselective synthesis of the brassinolide side chain involves the lactonlzation of Z-10 under acidic condition to give an @,p-unsa-'h, COzH a.6 C

πŸ“œ SIMILAR VOLUMES

A concise and stereoselective synthesis
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✍ Lizeng Peng; Yulin Li; WeidongZ Li πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 133 KB

A stereoselective synthesis of brassinolide, which involves construction of the side chain by highly stereoselective aldol reaction of 20S-6b-methoxy-3a,5-cyclo-5a-pregnane-20-carboxadehyde 5 with the anion of a-silyloxy ketone 6 is described.

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The brassinolide side chain was produced by the addition of (E)-propenyllithium to the C-22 aldehyde 2, followed by Sharpless epoxidation and epoxide opening with i-Pr2CuCNLi 2. Brassinolide 1(!) is a potent plant growth-promoter that was discovered by Grove et al. in 1979. 2 Its biological activit