Polyol synthesis through hydrocarbon oxidation: De novo synthesis of L-galactose

被引：62

作者：

Covell, Dustin J.

Vermeulen, Nicolaas A.

Labenz, Nathan A.

White, M. Christina ^{[1
]}

机构：

[1] Univ Illinois, Roger Adams Lab, Dept Chem, Urbana, IL 61801 USA

[2] Harvard Univ, Cambridge, MA 02138 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 48期

关键词：

allylic oxidation; C-H activation; carbohydrates; enantioselectivity; polyols;

D O I：

10.1002/anie.200603321

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Carbohydrates from hydrocarbons : A hydrocarbon oxidation strategy for the synthesis of chiral polyols is validated by the enantioselective, de novo synthesis of differentially protected L-galactose (see scheme, TBS = tert-butyldimethylsilyl, Bn = benzyl). Key to this strategy is the selective C-H oxidation method for transforming protected chiral allylic alcohols into (E)-2-butene-1,4-diol derivatives. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：8217 / 8220

页数：4

相关论文

共 47 条

[1]

[Anonymous], 2003, ANGEW CHEM

[2] REMOTE OXIDATION OF STEROIDS BY PHOTOLYSIS OF ATTACHED BENZOPHENONE GROUPS [J].

BRESLOW, R ;

BALDWIN, S ;

FLECHTNE.T ;

KALICKY, P ;

LIU, S ;

WASHBURN, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) :3251-3262

[3] A general model for selectivity in olefin cross metathesis [J].

Chatterjee, AK ;

Choi, TL ;

Sanders, DP ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370

[4] Serial ligand catalysis: A highly selective allylic C-H oxidation [J].

Chen, MS ;

Prabagaran, N ;

Labenz, NA ;

White, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6970-6971

[5] A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation [J].

Chen, MS ;

White, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) :1346-1347

[6] THE APPLICATION OF A MECHANISTIC MODEL LEADS TO THE EXTENSION OF THE SHARPLESS ASYMMETRIC DIHYDROXYLATION TO ALLYLIC 4-METHOXYBENZOATES AND CONFORMATIONALLY RELATED AMINE AND HOMOALLYLIC ALCOHOL DERIVATIVES [J].

COREY, EJ ;

GUZMANPEREZ, A ;

NOE, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :10805-10816

[7] Enantioselective total synthesis of FD-891 [J].

Crimmins, MT ;

Caussanel, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (10) :3128-3129

[8] C-C bond formation via C-H bond activation: Synthesis of the core of teleocidin B4 [J].

Dangel, BD ;

Godula, K ;

Youn, SW ;

Sezen, B ;

Sames, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) :11856-11857

[9] Chiral phosphoramide-catalyzed enantioselective addition of allylic trichlorosilanes to aldehydes. Preparative studies with bidentate phosphorus-based amides [J].

Denmark, SE ;

Fu, JP ;

Lawler, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) :1523-1536

[10] Diastereoselective synthesis of all eight L-hexoses from L-ascorbic acid [J].

Ermolenko, L ;

Sasaki, NA .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (02) :693-703

← 1 2 3 4 5 →