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A concise and stereoselective synthesis of the brassinolide and related compounds’ side chains

✍ Scribed by Lizeng Peng; Yulin Li; WeidongZ Li

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
133 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

📜 SIMILAR VOLUMES

A concise synthesis of the brassinolide
A concise synthesis of the brassinolide side chain
✍ Thomas G. Back; Peter G. Blazecka; M. Vijaya Krishna 📂 Article 📅 1991 🏛 Elsevier Science 🌐 French ⚖ 82 KB

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