Synthetic studies on terpenoids. Part XVI. Synthesis of 3β,17-diacetoxyphyllocladen-15-one
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2083-2088
- https://doi.org/10.1039/p19730002083
Abstract
A stereoselective synthesis of 3β,17-diacetoxyphyllocladen-15-one (XIX) from ethyl 5,5-ethylenedioxy-2-oxo-cyclohexanecarboxylate proceeding in ten stages via methyl 13,13-ethylenedioxy-3-oxopodocarpa-5,9(11)-diene-8β-carboxylate (V) and methyl 3β-hydroxy-13-oxopodocarpane-8β-carboxylate (XII) is described. The ester (XII) has been correlated with a known degradation product from phyllocladene. Some by-products from the hydrogenation of the diene (V) are discussed.Keywords
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