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Preparation of kaurenolide and its 5 alpha 6 alpha h isomer


, : Preparation of kaurenolide and its 5 alpha 6 alpha h isomer. Journal of the Chemical Society Perkin Transactions I (2): 517-520

In the preparation of kaurenolide [a fungal metabolite], essentially by the literature method, the formation of ent-6-oxokaur-16-en-19-oic acid from the toluene-p-sulfonate of 7.beta.-hydroxykaurenolide was dependent on the quality of the lithium iodide monohydrate used. ent-6-Hydroxykaura-6,16-dien-19-oic acid 19,6-lactone, prepared from the toluene-p-sulfonate of 7.beta.-hydroxykaurenolide, zinc dust and sodium iodide in refluxing 2-methoxyethanol, was hydrolyzed by base to ent-6-oxo-5.beta.-kaur-16-en-19-oic acid, which gave the 5.alpha.,6.alpha.(H) isomer of kaurenolide upon reduction.

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