A short practical synthesis of 2′-deoxymugineic acid

AbstractIron (Fe) is an essential nutrient, but is poorly bioavailable because of its low solubility in alkaline soils; this leads to reduced agricultural productivity. To overcome this problem, we first showed that the soil application of synthetic 2′-deoxymugineic acid, a natural phytosiderophore from the Poaceae, can recover Fe deficiency in rice grown in calcareous soil. However, the high cost and poor stability of synthetic 2′-deoxymugineic acid preclude its agricultural use. In this work, we develop a more stable and less expensive analog, proline-2′-deoxymugineic acid, and demonstrate its practical synthesis and transport of its Fe-chelated form across the plasma membrane by Fe(III)•2’-deoxymugineic acid transporters. Possibility of its use as an iron fertilizer on alkaline soils is supported by promotion of rice growth in a calcareous soil by soil application of metal free proline-2’-deoxymugineic acid.

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A Practical Synthesis of the Phytosiderophore 2′-Deoxymugineic Acid: A Key to the Mechanistic Study of Iron Acquisition by Graminaceous Plants

Angewandte Chemie International Edition ◽

10.1002/anie.200702403 ◽

2007 ◽

Vol 46 (37) ◽

pp. 7060-7063 ◽

Cited By ~ 30

Author(s):

Kosuke Namba ◽

Yoshiko Murata ◽

Manabu Horikawa ◽

Takashi Iwashita ◽

Shoichi Kusumoto

Keyword(s):

Iron Acquisition ◽

Mechanistic Study ◽

Deoxymugineic Acid ◽

Practical Synthesis ◽

Graminaceous Plants

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A Practical Synthesis of the Phytosiderophore 2′-Deoxymugineic Acid: A Key to the Mechanistic Study of Iron Acquisition by Graminaceous Plants

Angewandte Chemie ◽

10.1002/ange.200702403 ◽

2007 ◽

Vol 119 (37) ◽

pp. 7190-7193 ◽

Cited By ~ 6

Author(s):

Kosuke Namba ◽

Yoshiko Murata ◽

Manabu Horikawa ◽

Takashi Iwashita ◽

Shoichi Kusumoto

Keyword(s):

Iron Acquisition ◽

Mechanistic Study ◽

Deoxymugineic Acid ◽

Practical Synthesis ◽

Graminaceous Plants

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Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

Revista de Chimie ◽

10.37358/rc.17.1.5415 ◽

2017 ◽

Vol 68 (1) ◽

pp. 180-185

Author(s):

Adriana Maria Andreica ◽

Lucia Gansca ◽

Irina Ciotlaus ◽

Ioan Oprean

Keyword(s):

Sex Pheromone ◽

Coupling Reaction ◽

Coupling Scheme ◽

Lithium Aluminium Hydride ◽

Terminal Alkyne ◽

Mercury Derivative ◽

Lithium Aluminium ◽

Convenient Synthesis ◽

Practical Synthesis ◽

Insect Sex

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

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A practical synthesis of antheridiol

Tetrahedron Letters ◽

10.1016/s0040-4039(01)84904-2 ◽

1972 ◽

Vol 13 (26) ◽

pp. 2673-2676 ◽

Cited By ~ 3

Author(s):

T.C. McMorris ◽

T. Arunachalam ◽

R. Seshadri

Keyword(s):

Practical Synthesis

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Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions

Molecules ◽

10.3390/molecules26071897 ◽

2021 ◽

Vol 26 (7) ◽

pp. 1897

Author(s):

Hideyasu China ◽

Nami Kageyama ◽

Hotaka Yatabe ◽

Naoko Takenaga ◽

Toshifumi Dohi

Keyword(s):

Aqueous Solution ◽

Room Temperature ◽

Practical Method ◽

Hypervalent Iodine ◽

Mild Conditions ◽

Sequential Procedures ◽

Iodine Compounds ◽

Practical Synthesis ◽

Iodosobenzoic Acid ◽

Lower Temperature

We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone® in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound.

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