Novel rearrangement of 2-α-isopropyl-8-oxabicyclo[3.2.1]oct-6-ene producing the monoterpene 3-hydroxyphellandral
作者： Luiz Claudio de Almeida Barbosa , Antonio J. Demuner , John Mann , Dorila P. Veloso
DOI: 10.1039/P19930000585
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摘要: We describe a five-step synthesis of 2-α-isopropyl-8-oxabicyclo[3.2.1]oct-6-ene from 1,1,3, 3-tetrabromo-4-methylpentan-2-one, and its unexpected rearrangement to yield trans-3- hydroxy-4-isopropylcyclohex-1-enecarbaldehyde (3-hydroxyphellandral).
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sci-hub.se 参考文章(4)
John Mann, Helen J. Holland (née Overton), Terrence Lewis, Cycloaddition reactions of polysubstituted furans with oxyallyl carbocations Tetrahedron. ,vol. 43, pp. 2533- 2542 ,(1987) , 10.1016/S0040-4020(01)81660-4
John Mann, Helen J. Overton, Terence Lewis, Synthetic utility of oxyallyls: preparation of an analogue of helminthosporic acid Tetrahedron Letters. ,vol. 26, pp. 6133- 6136 ,(1985) , 10.1016/S0040-4039(00)95106-2
Derek H. R. Barton, Stuart W. McCombie, A new method for the deoxygenation of secondary alcohols Journal of the Chemical Society, Perkin Transactions 1. ,vol. 6, pp. 1574- 1585 ,(1975) , 10.1039/P19750001574
J. R. Malpass, N. J. Tweddle, Reaction of chlorosulphonyl isocyanate with 1,3-dienes. Control of 1,2- and 1,4-addition pathways and the synthesis of aza- and oxa-bicyclic systems Journal of the Chemical Society, Perkin Transactions 1. ,vol. 8, pp. 874- 884 ,(1977) , 10.1039/P19770000874