Polycyclic hydroxyquinones .29. Regioselective reactions of 5-sulphur-substituted furan-2(5H)-one anions with naphthoquinone monoketals. Application to the synthesis of anthracyclinone precursors

被引：13

作者：

Asenjo, P ^{[1
]}

Farina, F ^{[1
]}

Martin, MV ^{[1
]}

Paredes, MC ^{[1
]}

Soto, JJ ^{[1
]}

机构：

[1] CSIC,INST QUIM ORGAN GEN,E-28006 MADRID,SPAIN

来源：

TETRAHEDRON | 1997年 / 53卷 / 05期

关键词：

D O I：

10.1016/S0040-4020(96)01100-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The anions of furanones 7-10, reacted with naphthoquinone monoketals 11-15 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.

引用

页码：1823 / 1842

页数：20

共 41 条

[1] 1,3-dipolar cycloaddition of nitrile oxides to 2(5H)-furanones substituted at the 5-position by sulphur bearing groups [J].