Synthesis of analogues of griseusin A

被引：22

作者：

Brimble, MA ^{[1
]}

Nairn, MR ^{[1
]}

Park, J ^{[1
]}

机构：

[1] Univ Sydney, Sch Chem, Camperdown, NSW 2006, Australia

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 09期

关键词：

D O I：

10.1021/ol991020c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The synthesis of pyranonaphthoquinone-spiroacetals (3 and 4), which are synthetic analogues of the pyranonaphthoquinone antibiotic griseusin A (1) is reported. The oxygenated substituents on the spiroacetal ring were introduced onto the key naphthalene intermediate (5) using an anti asymmetric aldol reaction. The pyranonaphthoquinone skeleton was then assembled via furofuran annulation to naphthoquinone (22) to construct a furonaphthofuran ring followed by oxidative rearrangement to the furonaphthopyran ring.

引用

页码：1459 / 1462

页数：4

共 23 条

[1]

BIGI F, 1990, GAZZ CHIM ITAL, V120, P413

[2] HIGHLY REGIOSELECTIVE AND DIASTEREOSELECTIVE FRIEDEL-CRAFTS ALKYLATION OF PHENOLS WITH ALPHA-AMINO ALDEHYDES - SYNTHESIS OF OPTICALLY-ACTIVE EPHEDRINE-LIKE COMPOUNDS [J].

BIGI, F ;

CASNATI, G ;

SARTORI, G ;

ARALDI, G ;

BOCELLI, G .

TETRAHEDRON LETTERS, 1989, 30 (09) :1121-1124

[3] HIGHLY REGIOSELECTIVE AND DIASTEREOSELECTIVE FRIEDEL-CRAFTS ALKYLATION OF PHENOLS - SYNTHESIS OF 2-HYDROXYMANDELIC ESTERS [J].

BIGI, F ;

CASNATI, G ;

SARTORI, G ;

DALPRATO, C ;

BORTOLINI, R .

TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :861-864

[4]

Brimble M. A., 1996, MOLECULES, V1, P3, DOI [10.1007/S007830050002, DOI 10.1007/S007830050002]

[5] Pyranonaphthoquinone antibiotics - isolation, structure and biological activity [J].

Brimble, MA ;

Duncalf, LJ ;

Nairn, MR .

NATURAL PRODUCT REPORTS, 1999, 16 (03) :267-281

[6] Facile bisarylation of aldehydes using titanium naphtholates [J].

Brimble, MA ;

Oppen, E .

SYNTHETIC COMMUNICATIONS, 1997, 27 (06) :989-1007

[7] Synthesis of the monomeric unit of gamma-actinorhodin [J].

Brimble, MA ;

Duncalf, LJ ;

Phythian, SJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (09) :1399-1403

[8] SYNTHESIS OF 1-(2-HYDROXYARYL)-1,2,3-PROPANETRIOL AND 1-(2-HYDROXYARYL)-2-AMINO-1,3-PROPANEDIOL DERIVATIVES OF EITHER THREO OR ERYTHRO CONFIGURATION [J].

CASIRAGHI, G ;

CORNIA, M ;

RASSU, G .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :4919-4922

[9]

CASIRAGHI G, 1988, J ORG CHEM, V53, P1799

[10] STEREOSELECTIVE ARYLATIONS USING METAL PHENOLATES - COMPLEMENTARY SYNTHESIS OF 5-C-ARYLXYLOFURANOSE DERIVATIVES OF EITHER L-IDO OR D-GLUCO CONFIGURATION [J].

CORNIA, M ;

CASIRAGHI, G .

TETRAHEDRON, 1989, 45 (09) :2869-2874

← 1 2 3 →