Enantioselective Construction of Cis-2,6-Disubstituted Dihydropyrans: Total Synthesis of (-)-Centrolobine

被引：41

作者：

Chaladaj, Wojciech ^{[1
]}

Kowalczyk, Rafal ^{[2
]}

Jurczak, Janusz ^{[1
,3
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

[2] Wroclaw Univ Technol, Dept Organ Chem, Fac Chem, PL-50370 Wroclaw, Poland

[3] Warsaw Univ, Dept Chem, PL-02093 Warsaw, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 05期

关键词：

DIELS-ALDER REACTION; STEREOSELECTIVE-SYNTHESIS; HIGH-PRESSURE; CLAISEN REARRANGEMENT; ASYMMETRIC-SYNTHESIS; PRINS CYCLIZATIONS; CONCISE SYNTHESIS; FORMAL SYNTHESIS; TETRAHYDROPYRAN; 1-METHOXYBUTA-1,3-DIENE;

D O I：

10.1021/jo902167r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper presents a simple and efficient route to chiral cis-6-substituted 2-(2-hydroxyethyl)-5,6-dihydro-2H-pyrans, a versatile chiral building block. The strategy is based on three key transformations: enantioselective hetero-Diels-Alder (HDA) reaction of aldehyde with Danishekky's diene, selective reduction of carbonyl function, and Claisen or related rearrangement. The synthetic utility of the methodology is illustrated by toal synthesis of antibiotic (-)-centolobine.

引用

页码：1740 / 1743

页数：4

共 58 条

[1] Asymmetric hetero Diels-Alder reaction using chiral cationic metallosalen complexes as catalysts [J].

Aikawa, K ;

Irie, R ;

Katsuki, T .

TETRAHEDRON, 2001, 57 (05) :845-851

[2] Stereoselective synthesis of the monomeric unit of SCH 351448 [J].

Backes, J. Rene ;

Koert, Ulrich .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (12) :2777-2785

[3] DIANANE-CrIII-salen complexes as highly enantioselective catalysts for hetero-Diels-Alder reactions of aldehydes with dienes [J].

Berkessel, Albrecht ;

Vogl, Nadine .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (22) :5029-5035

[4] A ROUTE TO ARTIFICIAL GLYCOCONJUGATES AND OLIGOSACCHARIDES VIA ENZYMATICALLY RESOLVED GLYCALS - DRAMATIC EFFECTS OF THE HANDEDNESS OF THE SUGAR DOMAIN UPON THE PROPERTIES OF AN ANTHRACYCLINE DRUG [J].

BERKOWITZ, DB ;

DANISHEFSKY, SJ ;

SCHULTE, GK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) :4518-4529

[5] Synthesis of the C1-C21 (C1′-C21′) fragment of the dimeric polyketide natural product SCH 351448 [J].

Bhattacharjee, A ;

Soltani, O ;

De Brabander, JK .

ORGANIC LETTERS, 2002, 4 (04) :481-484

[6] A concise synthesis of (-)-centrolobine via a diastereoselective ring rearrangement metathesis-isomerisation sequence [J].

Böhrsch, V ;

Blechert, S .

CHEMICAL COMMUNICATIONS, 2006, (18) :1968-1970

[7] Efficient asymmetric synthesis of (+)-SCH 351448 [J].

Bolshakov, S ;

Leighton, JL .

ORGANIC LETTERS, 2005, 7 (17) :3809-3812

[8] Two successive one-pot reactions leading to the expeditious synthesis of (-)-centrolobine [J].

Boulard, L ;

BouzBouz, S ;

Cossy, J ;

Franck, X ;

Figadère, B .

TETRAHEDRON LETTERS, 2004, 45 (35) :6603-6605

[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] Claisen rearrangement over the past nine decades [J].

Castro, AMM .

CHEMICAL REVIEWS, 2004, 104 (06) :2939-3002

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