Ghatak, Usha Ranjan ; Ghosh, Subrata ; Sanyal, Baijayanti (1980) Synthetic studies towards complex diterpenoids. Part 13. Stereo-specific synthesis of intermediates to the diterpene alkaloids and the C20-gibberellins by a novel rearrangement of angularly fused cyclo-butanones Journal of the Chemical Society, Perkin Transactions 1, 1 . pp. 2881-2886. ISSN 0300-922X
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Official URL: http://www.rsc.org/publishing/journals/article.asp...
Related URL: http://dx.doi.org/10.1039/P19800002881
Abstract
A new stereospecific rearrangement of the saturated cyclobutanones (10a and b) and (11a and b) to the respective bridged cyclopentanones (2a and b) and (5a and b) using triethyloxonium tetrafluoroborate is described. Rearrangement studies of the specific labelled ketone [2H2]-(10a) indicate that the process is intramolecular. Sulphuric acid-catalysed rearrangement of (10a) produces the unsaturated methyl ketone (13). Transformation of the tetracyclic ketones (5a and b) to some angularly functionalised hydrofluorene synthons (14a and b) to the C20-gibberellins has been achieved.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 12321 |
| Deposited On: | 10 Nov 2010 05:43 |
| Last Modified: | 16 Feb 2011 07:16 |
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