Stereocontrolled synthesis of the brassinolide side-chain: formal synthesis of brassinolide
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1503-1507
- https://doi.org/10.1039/p19880001503
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.This publication has 6 references indexed in Scilit:
- Synthesis and biological activity of brassinolide and its 22β,23β-isomer: Novel plant growth-promoting steroidsPublished by Elsevier ,2003
- One-step stereochemical determination of four contiguous acyclic chiral centers on a steroidal side chain: a novel synthesis of brassinolideJournal of the American Chemical Society, 1986
- Stereocontrolled synthesis of 2-deoxycrustecdysone and related compoundsThe Journal of Organic Chemistry, 1986
- Stereoselective synthesis of the 20-hydroxyecdysone side chainJournal of the Chemical Society, Perkin Transactions 1, 1985
- Stereoselective synthesis of plant growth-prompting steroids, brassinolide, castasterone, typhasterol, and their 28-nor analoguesJournal of the Chemical Society, Perkin Transactions 1, 1984
- Synthesis of castasterone and its 22S,23S-isomer : two plant growth promoting ketonesJournal of the Chemical Society, Perkin Transactions 1, 1983