By Kenji Mori
Content material: creation : biofunctional molecules and natural synthesis -- Synthesis of phytohormones, phytoalexins, and different biofunctional molecules of plant starting place -- Synthesis of insect bioregulators except pheromones -- Synthesis of pheromones -- Synthesis of biofunctional molecules of microbial beginning -- Synthesis of marine bioregulators, medicinals and comparable compounds -- artificial exam of incorrectly proposed buildings of biomolecules -- end : technology as a human undertaking
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Extra info for Chemical Synthesis of Hormones, Pheromones and Other Bioregulators (Postgraduate Chemistry)
4). 17,18 (+)-Epigibberic acid (18) was obtained by Cross in 1954 by treating gibberellin A3 with hot mineral acid. Its absolute conﬁguration at C-9 is the same as that of the gibberellins. I therefore surmised that a synthesis of (±)-epigibberic acid (18) might be extended to the synthesis of the gibberellins. My idea as a young chemist with almost no experience was to synthesize the tetracyclic gibberellane system one by one, starting from the ring A. 5. Intramolecular Friedel–Crafts acylation of B followed by esteriﬁcation yielded bicyclic keto ester C.
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. 27. ; Sumiki, Y. Agric. Biol. Chem. 1961, 25 , 902–906. 28. ; Zschunke, A. Pharmazie 1979, 34 , 22–25. 2 Synthesis of Phytohormones, Phytoalexins and Other Biofunctional Molecules of Plant Origin Since ancient times, mankind has utilized higher plants as the sources of foods, clothes, houses, medicinals and so on, which are indispensable for mankind’s existence on this planet.
In 1956 Cross in the UK proposed structure A with C-19 → C-2 γ-lactone ring for Synthesis of Phytohormones, Phytoalexins and Other Biofunctional Molecules of Plant Origin O H 1 2 CO HO X 3 H CO2H Gibberellin A1 Gibberellin A4 X = OH X= H 20 H 11 10 H 12 9 C 5 B 8 14 13 D H 6 18 19 7 15 16 A 4 HO2C 17 H CO2H Gibberellin A12 ent -Gibberellane CO O O CO O CO OH HO HO 21 O CO HO HO CO2H A 1956 B. E. Cross B 1958 N. Takahashi C 1959 B. E. Cross D 1960 N. 2 Structures of the gibberellins. 10 Takahashi et al.