Recent advances in the synthesis of angucyclines

被引：73

作者：

Carreño, MC ^{[1
]}

Urbano, A ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

SYNLETT | 2005年 / 01期

关键词：

D O I：

10.1055/s-2004-834813

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The different strategies recently reported to construct the tetracyclic skeleton of angucyclines are presented: Diels-Alder and Friedel-Crafts reactions, nucleophilic additions, free radical annulations, rearrangements of cyclobutenones and cobalt-mediated [2+2+2] cycloadditions. Among the asymmetric approaches, the most efficient corresponds to Diels-Alder reactions including the use of chiral catalysts, enantiopure vinyl cyclohexenes as dienes, synthesized from quinic acid or (S,S)-[(p-tolylsulfinyl)methyl]-p-quinol, and chiral dienophiles such as (S,S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones. 1 Introduction 2 Diels-Alder Reactions 2.1 Formation of B Ring: DC+A Strategy 2.2 Formation of C Ring: D+BA Strategy 2.3 Formation of D Ring from a Dienophile Bearing the CBA Moiety 3 Friedel-Crafts Reactions 4 Nucleophilic Additions 4.1 Anionic Annulations with Phthalides 4.2 Other Anionic Annulations 5 Free Radical Annulations 6 Rearrangements of Cyclobutenones 7 Cobalt-Mediated [2+2+2] Cycloadditions 8 Summary.

引用

页码：1 / 25

页数：25

共 82 条

[1] Seitomycin:: Isolation, structure elucidation and biological activity of a new angucycline antibiotic from a terrestrial streptomycete [J].

Abdelfattah, M ;

Maskey, RP ;

Asolkar, RN ;

Grün-Wollny, I ;

Laatsch, H .

JOURNAL OF ANTIBIOTICS, 2003, 56 (06) :539-542

[2] OPTICALLY ACTIVE SULFOXIDES . SYNTHESIS + ROTATORY DISPERSION OF SOME DIARYL SULFOXIDES [J].

ANDERSEN, KK ;

FOLEY, JW ;

GAFFIELD, W ;

PAPANIKOLAU, NE ;

PERKINS, RI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5637-+

[3] Synthetic approaches to the angucycline antibiotics.: A route to C-glycosidic benz[a] anthraquinones [J].

Andrews, FL ;

Larsen, DS ;

Larsen, L .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (01) :15-24

[4] SYNTHETIC APPROACHES TO THE ANGUCYCLINE ANTIBIOTICS - SYNTHESIS OF THE C-GLYCOSIDIC CD RING-SYSTEM [J].

ANDREWS, FL ;

LARSEN, DS .

TETRAHEDRON LETTERS, 1994, 35 (46) :8693-8696

[5] TOTAL SYNTHESIS OF THE ANGUCYCLINE ANTIBIOTICS URDAMYCINONE-B AND 104-2 VIA A COMMON SYNTHETIC INTERMEDIATE [J].

BOYD, VA ;

SULIKOWSKI, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (32) :8472-8473

[6] PREPARATION OF 2-DEOXY-BETA-C-ARYLGLYCOSIDES AND C-ARYLGLYCALS FROM CARBOHYDRATE LACTONES [J].

BOYD, VA ;

DRAKE, BE ;

SULIKOWSKI, GA .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :3191-3193

[7] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].

CARRENO, MC .

CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760

[8] Enantioselective access to 2,7-cis-disubstituted oxepanes:: Formal synthesis of (+)-isolaurepan [J].

Carreño, MC ;

Mazery, RD ;

Urbano, A ;

Colobert, F ;

Solladié, G .

ORGANIC LETTERS, 2004, 6 (02) :297-299

[9] From central to helical chirality:: Synthesis of P and M enantiomers of [5]helicenequinones and bisquinones from (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone [J].

Carreño, MC ;

García-Cerrada, S ;

Urbano, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (17) :4118-4131

[10] β-hydroxysulfoxides as chiral cyclic ketone equivalents:: enantioselective synthesis of polysubstituted cyclohexanones, cyclohexenones and cyclohexenediones [J].

Carreño, MC ;

Pérez-González, M ;

Ribagorda, M ;

Somoza, A ;

Urbano, A .

CHEMICAL COMMUNICATIONS, 2002, (24) :3052-3053

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