Journal of the Chemical Society. Perkin transactions I p. 672 - 678 (1981)
Update date:2022-09-26
Topics:
Bearder, John R.
Kirkwood, Paul S.
MacMillan, Jake
A high-yield conversion of gibberellin A3 to gibberellin A5 is described.With thionyl chloride, gibberellin A3 methyl ester gives mainly 1β-chlorogibberellin A5 methyl ester; the isomeric 3α-chloro-1-ene was the main product from the reaction with toluene-p-sulphonyl chloride and lithium chloride.Each product is reduced by tri-n-butylstannane and acetylated to give the same mixture of the 13-acetates of gibberellin A5 methyl ester and of the isomeric 1(10)-ene-19,2-lactone.Hydrolysis of gibberellin A5 methyl ester 13-acetate gives gibberellin A5 in 20percent overall yield from gibberellin A3. <1-2H1>Gibberellin A5 is obtained in the same way by using tri-n-butyl<2H1>stannane in the reduction step.Analogous chlorination products of gibberellin A7 methyl ester and of gibberellin A3 are described.
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Doi:10.1021/jo00191a034
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(1981)
