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By tetraoxobispidines, we refer to 2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonanes, a class of bicyclic compounds also commonly known as Guareschi imides. These bisimides embed the central sparteine BC-ring domain in a form amenable for the regio- and stereocontrolled annulation of rings A and D. For seminal studies relating to the synthesis of Guareschi imides, see: (a) J. Guthzeit, J. prakt. Chem., 1902, 2, 11. (b) I. Guareschi, Gazz. Chim. Ital., 1919, 49, 126. (c) G. A. R. Kon and J. F. Thorpe, J. Chem. Soc., 1919, 686. (d) A. I. Vogel, J. Chem. 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Hemiaminal (7) was obtained in variable \u03b1:\u03b2 anomeric ratios (from 5:1 <U><<\/U> \u03b1:\u03b2 <U><<\/U> 1:3), with the \u03b2-anomer (exo hydroxyl group) usually predominating. The isomers could be separated by careful column chromatography and were identified by 1H NMR analysis of the anomeric proton signal, as follows: 7\u03b1 \u03b4H (anomeric) = 5.24 (1H, d, J = 5.7 Hz) ppm; 7\u03b2\u03b4H (anomeric) = 5.22 (1H, bs) ppm."},{"key":"#cr-split#-10.3987\/COM-06-S(W)45-30.1","doi-asserted-by":"crossref","unstructured":"Sakurai-type allylation of acyl iminium ions, see: (a) P.-Q. Huang, B.-G. Wei, and Y.-P. Ruan, Synlett, 2003, 1663.","DOI":"10.1055\/s-2003-40988"},{"key":"#cr-split#-10.3987\/COM-06-S(W)45-30.2","doi-asserted-by":"crossref","unstructured":"(b) D. J. Adams, A. J. Blake, P. A. Cooke, C. D. Gill, and N. S. 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Inspection of molecular models reveals that the dihedral angle between vicinal bridgehead and CHN methine protons within the conformationally rigid core of 6 is almost exactly 90 \u00b0; J-coupling between these protons would therefore be expected to be of low magnitude (or absent altogether) in accordance with the Karplus relation."},{"key":"10.3987\/COM-06-S(W)45-36","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)10427-6"},{"key":"10.3987\/COM-06-S(W)45-37","doi-asserted-by":"publisher","DOI":"10.1021\/jf00112a048"},{"key":"10.3987\/COM-06-S(W)45-38","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(95)91890-D"},{"key":"10.3987\/COM-06-S(W)45-39","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemphys.2003.07.005"}],"container-title":["HETEROCYCLES"],"original-title":[],"language":"en","deposited":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T20:45:25Z","timestamp":1719261925000},"score":1,"resource":{"primary":{"URL":"https:\/\/triggered.stanford.clockss.org\/ServeContent?doi=10.3987%2Fcom-06-s%28w%2945"},"secondary":[{"URL":"https:\/\/triggered.edinburgh.clockss.org\/ServeContent?doi=10.3987%2Fcom-06-s%28w%2945","label":"edinburgh"}]},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006]]},"references-count":43,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2006]]}},"alternative-id":["COM-06-S(W)45"],"URL":"https:\/\/doi.org\/10.3987\/com-06-s(w)45","relation":{},"ISSN":["0385-5414"],"issn-type":[{"type":"print","value":"0385-5414"}],"subject":[],"published":{"date-parts":[[2006]]}}}