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handle: 10261/21930
Oxidación del epicandicandiol (I) con el reactivo de Jones dio el ácido 7-oxo-ent-kaur-16-en-18-oico. La autoxidación de este último da la 7-oxo-ent-kaur-5,16-dien-18,6-olida. Esta lacxtona se obtuvo con mejor rendimiento cuando se utilizó el ester metílico. Por reagrupamiento ácido bencílico de la $-lactona B-$ no saturada se obtuvo el hidroxy-ácido V con el esqueleto del gibbano, que por metilación dio el correspondiente dimetil ester (VI).
Oxidation of epicandicandiol (I) with Jones' reagent gave 7-oxo-ent-kaur-16-en-18-oic. Which was autoxidated to 7-oxo-ent-kaur-5,16-dien-18,6-olide (IV). Better yields of this lactone were obtained starting from the mrthyl ester. Benzilic acid rearrangement of the B-$-unsaturated-$-lactone IV gave the ring contracted hydroxy-acid V with the gibbane skeleton. Methylation of V yield the dimenthyl ester (VI).
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