1976
DOI: 10.1002/hlca.19760590503
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Synthesis of Abscisic Acid

Abstract: Suunrnary.A stereosclectivc synthesis of ( &)-abscisic acid (7) is described in which &cis 3-methylpent-2-en-4-yn-1-01 (2) is used t o introduce the 2-&, 4-tuans geonictry.Abscisic acid, a widely distributed natural plant-growth regulator [l] [a] is the dextrotatory (1's)-enantiomer of the 2-cis,4-trans acid 7 [ 3 ] . Its 2-trans,4-trans isomer is stated to have little or no biological activity, though both geometrical isomers are readily converted into an equilibrium mixture (ca. 1 :1) of the two forms on i… Show more

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Cited by 44 publications
(21 citation statements)
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“…The remaining steps in the synthesis of 8'-demethyl ABA closely follow those previously reported for the synthesis of ABA (14), with the exception of combining the alkyne addition and subsequent reduction of the triple bond into one step (see Fig. 2).…”
Section: Resultssupporting
confidence: 72%
“…The remaining steps in the synthesis of 8'-demethyl ABA closely follow those previously reported for the synthesis of ABA (14), with the exception of combining the alkyne addition and subsequent reduction of the triple bond into one step (see Fig. 2).…”
Section: Resultssupporting
confidence: 72%
“…A solution of 4c (1.09 g, 5 mmol) in THF (5 mL) was added slowly, the mixture was stirred for 0.5 h at -78 °C, and then it was warmed to room temperature and stirred for 2 h. The reaction was quenched with saturated aqueous NH 4 Cl solution (10 mL) and extracted with EtOAc (3 × 30 mL). The combined organics were washed with brine (2 × 20 mL), dried over anhydrous Na 2 SO 4 and concentrated.…”
Section: (Z)-4-hydroxy-4-(5′-hydroxy-3′-methylpent-3′-en-1′-yn-1′-yl)mentioning
confidence: 99%
“…(5′-hydroxy-3-methylpent-3′-en-1′-yn-1′-yl)-7,7-dimethyl-6,7-dihydroquinolin-8(5H)-one (6k): n-BuLi (4.2 mL, 10 mmol, 2.4 mol/L) was added dropwise to a solution of (Z)-3-methylpent-2-en-4-yn-1-ol (0.48 g, 5 mmol) in THF (10 mL) at −78 °C under a N 2 atmosphere, and then the mixture was stirred for 1 h at −78 °C. A solution of 4g (0.94 g, 5 mmol) in THF (5 mL) was added slowly, the mixture was stirred for 0.5 h at −78 °C, and then it was warmed to room temperature and stirred for 2 h. The reaction was quenched with saturated aqueous NH 4 Cl solution (10 mL) and extracted with EtOAc (3 × 30 mL). The combined organics were washed with brine (2 × 20 mL), dried over anhydrous Na 2 SO 4 and concentrated.…”
Section: (Z)-5-hydroxy-5-(5′-hydroxy-3′-methylpent-3′-en-1′-yn-1′-yl)mentioning
confidence: 99%
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