Chemical Synthesis of Hormones, Pheromones and Other by Kenji Mori

By Kenji Mori

Content material: advent : biofunctional molecules and natural synthesis -- Synthesis of phytohormones, phytoalexins, and different biofunctional molecules of plant foundation -- Synthesis of insect bioregulators except pheromones -- Synthesis of pheromones -- Synthesis of biofunctional molecules of microbial starting place -- Synthesis of marine bioregulators, medicinals and comparable compounds -- artificial exam of incorrectly proposed constructions of biomolecules -- end : technological know-how as a human activity

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The corresponding acetate was epoxidized with m-chloroperbenzoic acid to give epoxides I and J. The epoxide J was converted to (S )-dehydrovomifoliol (29), while I yielded (R)-29. 21 Major members of the naturally occurring brassinosteroids. 21). They are called brassinosteroids. 2 Synthesis of (22S ,23S ,24S )-28-homobrassinolide In late 1979, Professor Marumo of Nagoya University requested me to synthesize brassinolide or its analog as soon as possible. 65 Stigmasterol, an abundant phytosterol of soybeans, was employed as the starting material, and the product 36 showed plant-growth-promoting activity, although it was about 1% of brassinolide itself.

16. J. Tetrahedron Lett. 1976, 2055–2058. 17. G. Tetrahedron Lett. 1992, 33 , 891–894. 18. ; Ando, T. Tetrahedron Lett. 2001, 42 , 687–689. 19. M. Nature 2002, 415 , 545–549. 20. J. Pure Appl. Chem. 1967, 14 , 19–37. 21. -M. The Logic of Chemical Synthesis, Wiley; New York, 1989, pp. 1–436. 22. E. J. Chem. Soc. 1956, 530–534. 23. ; Nakagawa, K. Tetrahedron 1986, 42 , 523–528. 24. A. Tetrahedron Lett. 1972, 2999–3002. 25. Mori, K. Tetrahedron 1974, 30 , 3807–3810. 26. A. Tetrahedron 1977, 33 , 1845–1889.

The desired product E was isolated after chromatographic purification (by preparative GC in initial experiments and by conventional SiO2 chromatography in later experiments) as crystals. Subsequent reprotection of the ring D-ketone afforded F, whose reduction with sodium borohydride was followed by catalytic hydrogenation to give G. The lactone in ring A was constructed by treating G with dilute sulfuric acid. After methylation of the ring B carboxyl group, H was obtained. 24,25 Gibberellin C with plant-growth-promoting activity was thus synthesized from B.

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