Asymmetric synthesis of the tetrahydropyran ring, C32-C38 fragment, of phorboxazoles

被引：23

作者：

Brinkmann, Y

Carreño, MC

Urbano, A

Colobert, F

Solladié, G

机构：

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

[2] Univ Strasbourg, Lab Stereochim, CNRS, ECPM, F-67087 Strasbourg 2, France

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 23期

关键词：

D O I：

10.1021/ol048099s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of a model aldehyde (2R,6R)-2 and the C32-C38 fragment of phorboxazoles, (2R,4R,6R)-1, is described using a sulfoxide as chiral auxiliary. Key advances include the stereoselective reductions of beta-keto- or beta,gamma-diketosulfoxides, the acid-catalyzed cyclization of enantiopure sulfinyl hydroxy ketone precursors to the tetrahydropyran ring, and the Pummerer reaction on the pendant sulfoxide to create the formyl group.

引用

收藏

页码：4335 / 4338

页数：4

相关论文

共 45 条

[1] Convergent synthesis of the C31-C46 domain of the phorboxazole natural products [J].

Ahmed, F ;

Forsyth, CJ .

TETRAHEDRON LETTERS, 1998, 39 (3-4) :183-186

[2] CONVENIENT SYNTHESIS OF TRIACETIC ACID METHYL-ESTER [J].

BATELAAN, JG .

SYNTHETIC COMMUNICATIONS, 1976, 6 (02) :81-83

[3] Convergent highly stereoselective preparation of the C12-C24 fragment of macrolactin A [J].

Bonini, C ;

Chiummiento, L ;

Pullez, M ;

Solladié, G ;

Colobert, F .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :5015-5022

[4] Efficient synthesis of (-)-trans-kumausyne via tandem intramolecular alkoxycarbonylation-lactonization [J].

Boukouvalas, J ;

Fortier, G ;

Radu, II .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :916-917

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

CARRENO, MC .

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

[6] Synthesis and trimethylaluminum additions on γ-hydroxy-δ-sulfinyl and sulfonyl enoates [J].

Carreño, MC ;

Sanz-Cuestat, MJ ;

Colobert, F ;

Solladié, G .

ORGANIC LETTERS, 2004, 6 (20) :3537-3540

[7] 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

[8] Influence of diene substitution on Diels-Alder reactions between vinyl dihydronaphthalenes and (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone [J].

Carreño, MC ;

García-Cerrada, S ;

Sanz-Cuesta, MJ ;

Urbano, A .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4315-4321

[9] Reductive cyclizations of hydroxysulfinyl ketones:: Enantioselective access to tetrahydropyran and tetrahydrofuran derivatives [J].

Carreño, MC ;

Des Mazery, R ;

Urbano, A ;

Colobert, F ;

Solladié, G .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7779-7787

[10] 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

← 1 2 3 4 5 →