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Paper | Regular issue | Vol 48, No. 11, 1998, pp.2245-2251
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8288
Improved Procedures for Direct Conversions of Natural 3β-Hydroxy-gibberellins to 3α-Hydroxy-and 3-Oxo-gibberellins

Hideharu Seto,* Shozo Fujioka, Yuji Kamiya, and Shigeo Yoshida

*The Institute of Physical and Chemical Research, Wako-shi, Saitama 351-0198, Japan


Natural 3β-hydroxy-gibberellins, GA3 (gibberellic acid) (1), GA1 (2), and GA4 (3), were directly converted to 3α-hydroxy-gibberellins, 3-epi-GA3 (4), -GA1 (5) and -GA4 (6), by highly α-biased equilibration through retro- and realdol mechanism with potassium tert-butoxide in tert-butyl alcohol, and to 3-oxo-gibberellins, 3-oxo-GA95 (7), -GA20 (8) and -GA9 (9), by catalytic oxidation with tetrapropylammonium perruthenate.