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
Stereocontrolled synthesis of the brassinolide side chain via a pyranone derivative
β Scribed by Tetsuji Kametani; Katsuyuki Keino; Masaharu Kigawa; Masayoshi Tsubuki; Toshio Honda
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 151 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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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.