Abstract
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 20% 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.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
