POLYCYCLIC HYDROXYQUINONES .29. REGIOSELECTIVE REACTIONS OF 5-SULFUR-SUBSTITUTED FURAN-2(5H)-ONE ANIONS WITH NAPHTHOQUINONE MONOKETALS - APPLICATION TO THE SYNTHESIS OF ANTHRACYCLINONE PRECURSORS

Authors
ASENJO P FARINA F MARTIN MV PAREDES MC SOTO JJ
Citation
P. Asenjo et al., POLYCYCLIC HYDROXYQUINONES .29. REGIOSELECTIVE REACTIONS OF 5-SULFUR-SUBSTITUTED FURAN-2(5H)-ONE ANIONS WITH NAPHTHOQUINONE MONOKETALS - APPLICATION TO THE SYNTHESIS OF ANTHRACYCLINONE PRECURSORS, Tetrahedron, 53(5), 1997, pp. 1823-1842
Citations number
41
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
5
Year of publication
1997
Pages
1823 - 1842
Database
ISI
SICI code
0040-4020(1997)53:5<1823:PH.RRO>2.0.ZU;2-S
Abstract
The anions of furanones 7-10, reacted with naphthoquinone monoketals 1 1-15 to afford exclusively the C-5 substituted Michael adducts in good yield The annelation reactions of the anions generated from furanones 30 and 33 with naphthoquinone monoketals 11 and 12 lead to 2-sulphur- substituted 1,4-anthraquinones 32, 35 and 36. Diels-Alder reaction of the 1,4-anthraquinones 41 and 42 with (E)-1,3-bis[(trimethylsilyl)oxy] buta-1,3-diene (37) affords ABCD tetracyclic systems related to those existing in anthracyclinones. (C) 1997, Elsevier Science Ltd.