TY - JOUR
T1 - Synthesis and conjugate additions of 2,3,4,9-tetrahydro-1H-xanthene-1,9-diones
AU - Gabbutt, Christopher D.
AU - Hepworth, John D.
AU - Urquhart, Michael W.J.
AU - Vazquez De Miguel, Luis Millan
PY - 1997/6/21
Y1 - 1997/6/21
N2 - An efficient two step procedure for the synthesis of 2,3,4,9-tetrahydro-1H-xanthene-1,9-diones is described. A study of their conjugate additions has shown them to be efficient Michael acceptors. Reaction of 2,3,4,9-tetrahydro-1H-xanthene-1,9-dione with tris(methylthio)methyllithium, followed by mercury(II) catalysed methanolysis, gave methyl 1-hydroxy-9-oxo-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylate, the nucleus of the secalonic acids and other natural products.
AB - An efficient two step procedure for the synthesis of 2,3,4,9-tetrahydro-1H-xanthene-1,9-diones is described. A study of their conjugate additions has shown them to be efficient Michael acceptors. Reaction of 2,3,4,9-tetrahydro-1H-xanthene-1,9-dione with tris(methylthio)methyllithium, followed by mercury(II) catalysed methanolysis, gave methyl 1-hydroxy-9-oxo-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylate, the nucleus of the secalonic acids and other natural products.
UR - http://www.scopus.com/inward/record.url?scp=33748596385&partnerID=8YFLogxK
U2 - 10.1039/a700375g
DO - 10.1039/a700375g
M3 - Article
AN - SCOPUS:33748596385
SP - 1819
EP - 1824
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
SN - 0300-922X
IS - 12
ER -