Synthesis of Gibberellin Ga(53) and Its (17,17-D-2)Derivative

Abstract

Gibberellin GA53 (1) has been prepared by a modified Wolff- Kishner reduction of gibberellin GA19 protected as its 13-methoxymethyl ether (11). Careful regulation of the temperature at c. 174° is necessary, otherwise migration of the 16-ene function into the endocyclic 15-ene position occurs to an increasing extent at higher temperatures. The methodology was also extended to the preparation of the (17,17-D2)derivative (20).