期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 6, 期 10, 页码 1831-1842出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/b801858h
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Two independent routes for the total synthesis of the bioactive neolignan ( - )-conocarpan are described. The first (98% ee) is based on formal radical cyclization onto a benzene ring, and involves a 5-exo-trigonal closure onto a double bond restrained within a 6-membered ring. The second route (88% ee), which is shorter, is based on 5-exo-trigonal cyclization of an aryl radical onto a pendant terminal double bond. The two routes differ in their degree of stereoselectivity. The absolute configuration originally assigned to (+)-conocarpan had previously been called into question on the basis of empirical chiroptical rules; the present chemical work confirms the need for revision, and the assigned absolute configurations of several compounds correlated with (+)-conocarpan must also be changed.
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