Convergent de novo synthesis of vineomycinone B2 methyl ester

被引：27

作者：

Chen, Qian ^{[1
]}

Zhong, Yashan ^{[2
]}

O'Doherty, George A. ^{[2
]}

机构：

[1] Guangdong Univ Technol, Guangzhou 510006, Guangdong, Peoples R China

[2] Northeastern Univ, Boston, MA 02115 USA

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 60期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; DIHYDROXYLATION; PORTION; MOIETY;

D O I：

10.1039/c3cc44050h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient de novo synthesis of vineomycinone B-2 methyl ester has been achieved. The longest linear route required only 14 steps from achiral commercially available startingmaterials (4.0% overall yield). The key transformations included the de novo asymmetric synthesis of two key fragments, whichwere joined by a convergent late stage Suzuki's glycosylation for the construction of the aryl beta-C-glycoside. A subsequent BBr3 one-pot debenzylation, demethylation and air oxidation provided vineomycinone B-2 methyl ester.

引用

页码：6806 / 6808

页数：3

共 33 条

[1] De novo synthesis of a galacto-papulacandin moiety via an iterative dihydroxylation strategy [J].

Ahmed, MM ;

O'Doherty, GA .

TETRAHEDRON LETTERS, 2005, 46 (24) :4151-4155

[2]

Andriy L., 2005, MOL BIOSYST, V1, P117

[3]

Babu R. S., 2005, J CARBOHYDR CHEM, P24

[4] Efficient synthesis of 5-aryl-2-vinylfurans by palladium catalyzed cross-coupling strategies [J].

Balachari, D ;

Quinn, L ;

O'Doherty, GA .

TETRAHEDRON LETTERS, 1999, 40 (26) :4769-4773

[5] Sharpless asymmetric dihydroxylation of 5-aryl-2-vinylfurans: Application to the synthesis of the spiroketal moiety of papulacandin D [J].

Balachari, D ;

O'Doherty, GA .

ORGANIC LETTERS, 2000, 2 (06) :863-866

[6] Enantioselective synthesis of the papulacandin ring system: Conversion of the mannose diastereoisomer into a glucose stereoisomer [J].

Balachari, D ;

O'Doherty, GA .

ORGANIC LETTERS, 2000, 2 (25) :4033-4036

[7] TOTAL SYNTHESIS OF VINEOMYCINONE-B2 METHYL-ESTER VIA DOUBLE BRADSHER CYCLIZATION [J].

BOLITT, V ;

MIOSKOWSKI, C ;

KOLLAH, RO ;

MANNA, S ;

RAJAPAKSA, D ;

FALCK, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6320-6321

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

Chen, Chi-Li ;

Sparks, Steven M. ;

Martin, Stephen F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (42) :13696-13697

[9] De Novo Asymmetric Synthesis of Fridamycin E [J].

Chen, Qian ;

Mulzer, Michael ;

Shi, Pei ;

Beuning, Penny J. ;

Coates, Geoffrey W. ;

O'Doherty, George A. .

ORGANIC LETTERS, 2011, 13 (24) :6592-6595

[10] TOTAL SYNTHESIS OF VINEOMYCINONE-B2 METHYL-ESTER [J].

DANISHEFSKY, SJ ;

UANG, BJ ;

QUALLICH, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1285-1293

← 1 2 3 4 →