An efficient stereospecific synthesis of the plant hormone (RS)-abscisic acid from the readily available 4-oxoisophorone, trimethylsilylacetylene and ethyl but-2-ynoate, is described.
see for example, (a) CornforthJ.W., MilborrowB. V., and RybackG., Nature, 1965, 206, 715; (b) D. L. Roberts, R. A. Heckman, B. P. Hege and S. A. Bellin, J. Org. Chem., 1968, 33, 3566; (c) M. Shibasaki, S. Terashima and S. Yamada, Chem. Pharm. Bull., 1976, 24, 315; (d) M. G. Constantino, P. M. Donate and N. Peragnani, J Org. Chem., 1986, 51, 253; (e) Sir John Cornforth, J. E. Hawes and R. Mallaby, Aust. J. Chem., 1992, 45, 179; (f) H. Kiyota, M. Nakabayashi and T. Oritani, Tetrahedron Asymmetry, 1999, 10, 3811; (g) T. Asami, K. Sekimata, J. M. Wang, K. Yoneyama, Y. Takeuchi and S. Yoshida, J Chem. Research (S), 1999, 658.
3.
MarxJ.N., and SondheimerF., Tetrahedron, 1966 Suppl. 8.1
4.
HornerL., and OedigerH., Chem. Ber., 1958, 91, 437.
5.
GoughS.T. D., and TrippettS., Proc. Chem. Soc., 1961, 302.
6.
TrostB.M., SorumM. T., ChanC., HarmsA. E., and RuhterG., J. Am. Chem. Soc., 1997, 119, 698.
7.
ChanleyJ.D., and SobotkaH., J. Am. Chem. Soc., 1940, 71, 4140.
8.
AttenburrowJ., CameronA. F. B., ChapmanJ. H., EvansR. M., HemsB. A., JansenA. B. A., and WalkerT., J. Chem. Soc., 1952, 1094.
9.
LeyS.V., NormanJ., GriffithW. P., and MarsdenS. P., Synthesis, 1994, 639.
10.
ThomasonS.C., and KublerD. G., J. Chem. Educ., 1968, 45, 546.
11.
MayerH.J., RigassiN., SchwieterU., and WeedonB. C. L., Helv. Chim. Acta, 1976, 59, 1424.
