C-aryl glycosides via tandem intramolecular benzyne-furan cycloadditions.: Total synthesis of vineomycinone B2 methyl ester

被引：72

作者：

Chen, Chi-Li ^{[1
]}

Sparks, Steven M. ^{[1
]}

Martin, Stephen F. ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 42期

关键词：

D O I：

10.1021/ja0652619

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A triply convergent total synthesis of vineomycinone B2 methyl ester has been achieved by an approach with a longest linear sequence of 16 steps. The synthesis features the use of silicon tethers as disposable linkers to control the regiochemistry in two tandem Diels-Alder reactions of substituted benzynes and glycosyl furans to provide rapid access to the fully intact anthrarufin core of vineomycinone B2 methyl ester. Copyright © 2006 American Chemical Society.

引用

页码：13696 / 13697

页数：2

共 26 条

[11] 3-ALKYLFURANS AS USEFUL SYNTHETIC EQUIVALENTS FOR SUBSTITUTED DELTA-2-BUTENOLIDES [J].

GOLDSMITH, D ;

LIOTTA, D ;

SAINDANE, M ;

WAYKOLE, L ;

BOWEN, P .

TETRAHEDRON LETTERS, 1983, 24 (52) :5835-5838

[12] TETRAHALOBENZENES AS DI-ARYNE EQUIVALENTS IN POLYCYCLIC ARENE SYNTHESIS [J].

HART, H ;

LAI, C ;

NWOKOGU, GC ;

SHAMOUILIAN, S .

TETRAHEDRON, 1987, 43 (22) :5203-5224

[13] THE STRUCTURE OF VINEOMYCIN-B-2 [J].

IMAMURA, N ;

KAKINUMA, K ;

IKEKAWA, N ;

TANAKA, H ;

OMURA, S .

JOURNAL OF ANTIBIOTICS, 1981, 34 (11) :1517-1518

[14]

JARAMILLO C, 1994, SYNTHESIS-STUTTGART, P1

[15] Regioselective synthesis of unsymmetrical C-aryl glycosides using silicon tethers as disposable linkers [J].

Kaelin, DE ;

Sparks, SM ;

Plake, HR ;

Martin, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (43) :12994-12995

[16] General strategies for the synthesis of the major classes of C-aryl glycosides [J].

Kaelin, DE ;

Lopez, OD ;

Martin, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6937-6938

[17]

Levy D.E., 1995, CHEM C GLYCOSIDES

[18] Synthesis of C-saccharides and higher congeners [J].

Liu, L ;

McKee, M ;

Postema, MHD .

CURRENT ORGANIC CHEMISTRY, 2001, 5 (12) :1133-1167

[19] Unified strategy for the synthesis of C-aryl glycosides [J].

Martin, SF .

PURE AND APPLIED CHEMISTRY, 2003, 75 (01) :63-70

[20] CONVERGENT TOTAL SYNTHESIS OF VINEOMYCINONE-B2 METHYL-ESTER AND ITS C(12)-EPIMER [J].

MATSUMOTO, T ;

KATSUKI, M ;

JONA, H ;

SUZUKI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :6982-6992

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