Total stereoselective synthesis of (+)-goniothalesdiol

被引：23

作者：

Carreño, MC

Hernández-Torres, G

Urbano, A

Colobert, F ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ C1, E-28049 Madrid, Spain

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

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 24期

关键词：

D O I：

10.1021/ol0523603

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of (+)-goniothalesdiol (1) was accomplished in nine steps starting from commercially available (-)-(2S,3s)dimethyl D-tartrate (3). The key features were a completely diastereoselective reduction of beta-ketosulfoxide to generate the stereogenic center at C-5 in 7 and formation of the 2,5-cis-substituted tetrahydrofuran ring in 10 from a stereoselective Et3SiH/TMSOTf-promoted reductive cyclization/ deoxygenation.

引用

收藏

页码：5517 / 5520

页数：4

相关论文

共 35 条

[1] Synthesis of (+)-goniothalesdiol and (+)-7-epi-goniothalesdiol [J].

Babjak, M ;

Kapitán, P ;

Gracza, T .

TETRAHEDRON, 2005, 61 (09) :2471-2479

[2] The first total synthesis of goniothalesdiol [J].

Babjak, M ;

Kapitán, P ;

Gracza, T .

TETRAHEDRON LETTERS, 2002, 43 (39) :6983-6985

[3] Efficient stereochemical controllers in biaryl Suzuki coupling reactions:: Benzylic carbinols bearing in β-position thioether, dimethylamino, or sulfoxide groups [J].

Broutin, PE ;

Colobert, F .

ORGANIC LETTERS, 2005, 7 (17) :3737-3740

[4] An asymmetric biaryl Suzuki cross-coupling reaction: Stereogenic benzylic carbinols as chiral auxiliaries [J].

Broutin, PE ;

Colobert, F .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (06) :1113-1128

[5] Styryl-lactone derivatives and alkaloids from Goniothalamus borneensis (Annonaceae) [J].

Cao, SG ;

Wu, XH ;

Sim, KY ;

Tan, BKH ;

Pereira, JT ;

Goh, SH .

TETRAHEDRON, 1998, 54 (10) :2143-2148

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

CARRENO, MC .

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

[7] Short asymmetric synthesis of (-)- and (+)-cis-lauthisan [J].

Carreño, MC ;

Des Mazery, R ;

Urbano, A ;

Colobert, F ;

Solladié, G .

ORGANIC LETTERS, 2005, 7 (10) :2039-2042

[8] Enantioselective synthesis of (+)- and (-)-dihydroepiepoformin and (+)-epiepoformin [J].

Carreño, MC ;

Merino, E ;

Ribagorda, M ;

Somoza, A ;

Urbano, A .

ORGANIC LETTERS, 2005, 7 (07) :1419-1422

[9] Efficient asymmetric synthesis of [7]helicene bisquinones [J].

Carreño, MC ;

González-López, M ;

Urbano, A .

CHEMICAL COMMUNICATIONS, 2005, (05) :611-613

[10] Recent advances in the synthesis of angucyclines [J].

Carreño, MC ;

Urbano, A .

SYNLETT, 2005, (01) :1-25

← 1 2 3 4 →