Tetrahedron p. 3259 - 3270 (1991)
Update date:2022-07-29
Topics: Asymmetric synthesis Retrosynthetic analysis Purification and characterization Introduction of Stereochemistry Scale-Up and Yield Optimization
Nelson, Lloyd A. K.
Shaw, Angela C.
Abrams, Suzanne R.
A total synthesis of 7'-hydroxyabscisic acid (1), a putative metabolite of the plant hormone abscisic acid (ABA), is described.The key intermediate in the twelve step synthesis is 2-t-butyldimethylsiloxymethyl-4,4-ethylenedioxy-6,6-dimethylcyclohex-2-en-1-one (5) which contains the desired masked hydroxyl group at the C-7'position of ABA.The final transformation in the synthesis, the hydrolysis of the methyl ester of 1 is readily accomplished with porcine liver esterase.Optically pure (+)- and (-)-forms of 1 are obtained by resolution of the silyl ether methyl ester by HPLC on a chiral column.
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Doi:10.1021/jo2015054
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