Allylic vs homoallylic control of stereospecificity in the epoxidation of 3(1′-hydroxyethyl)-5,8-dimethoxy-1,2-dihydronaphthalen-1-ol: implications for the synthesis of chiral anthracyclines |
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| Authors: | Robert W. Irvine Richard A. Russell Ronald N. Warrener |
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| Affiliation: | 1. Department of Chemistry. The Faculties, The Australian National University. GPO Box 4, Canberra, A.C.T. 2601, Australia;2. Department of Chemistry, Faculty of Military Studies, U.N.S.W., Duntroon, A.C.T. 2600. Australia |
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| Abstract: | The stereochemistry of the epcxidation of the title compound with t-BuOOH catalysed by VO(acac)2 is subject to exclusive homoallylic control. Secondary allylic alcohols in the side chain regain their normal controlling influence over diastereoselection only when the homoallylic group is blocked. |
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