Synthetic studies on terpenoids. Part XVI. Synthesis of 3β,17-diacetoxyphyllocladen-15-one

Mukherjee, Debabrata ; Mukhopadhyay, Sunil Kumar ; Mahalanabis, Kumur Kanti ; Gupta, Amitabha Das ; Dutta, Phanindra Chandra (1973) Synthetic studies on terpenoids. Part XVI. Synthesis of 3β,17-diacetoxyphyllocladen-15-one Journal of the Chemical Society Perkin Transactions 1 . pp. 2083-2088. ISSN 1472-7781

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Official URL: http://www.rsc.org/publishing/journals/article.asp...

Related URL: http://dx.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.

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Deposited On:20 Nov 2010 14:34
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