TY - JOUR
T1 - A new synthesis of anthraquinones using dihydro-oxazoles and Grignard reagents derived from Mg(Anthracene)(THF)31
AU - Nicoletti, Teresa M.
AU - Raston, Colin L.
AU - Sargent, Melvyn V.
PY - 1990/1
Y1 - 1990/1
N2 - A general synthesis of anthraquinones which depends on the displacement of the methoxy group from an o-methoxyaryldihydro-oxazole by a methoxy substituted benzylmagnesium chloride, generated by using a magnesium-anthracene complex, has been developed. The masked benzyl-benzoic acids which result from these reactions are deprotected and then ring-closed to anthrones which on oxidation yield anthraquinones. In this way, the following naturally occurring anthraquinones (or derivatives thereof have been synthesized): chrysophanol (9), islandicin (19), digitopurpone (21), tri-O-methylemodin (26), and di-O-methylsoranjidiol (29).
AB - A general synthesis of anthraquinones which depends on the displacement of the methoxy group from an o-methoxyaryldihydro-oxazole by a methoxy substituted benzylmagnesium chloride, generated by using a magnesium-anthracene complex, has been developed. The masked benzyl-benzoic acids which result from these reactions are deprotected and then ring-closed to anthrones which on oxidation yield anthraquinones. In this way, the following naturally occurring anthraquinones (or derivatives thereof have been synthesized): chrysophanol (9), islandicin (19), digitopurpone (21), tri-O-methylemodin (26), and di-O-methylsoranjidiol (29).
UR - http://www.scopus.com/inward/record.url?scp=37049068587&partnerID=8YFLogxK
U2 - 10.1039/P19900000133
DO - 10.1039/P19900000133
M3 - Article
AN - SCOPUS:37049068587
SP - 133
EP - 138
JO - Journal of the Chemical Society. Perkin Transactions 1
JF - Journal of the Chemical Society. Perkin Transactions 1
SN - 1472-7781
IS - 1
ER -