Approach to the eleutherobin core:: Synthesis of a key intermediate by intramolecular Diels-Alder cycloaddition

被引：13

作者：

Bruyere, Helene ^{[1
]}

Dos Reis, Catarina ^{[1
]}

Samaritani, Simona ^{[1
]}

Ballereau, Stephanie ^{[1
]}

Royer, Jacques ^{[1
]}

机构：

[1] Univ Paris 05, CNRS, UMR 8638, Fac Pharm, F-75270 Paris 06, France

来源：

SYNTHESIS-STUTTGART | 2006年 / 10卷 / 10期

关键词：

aldol reactions; Diels-Alder reactions; antitumor agents; eleuthesides; diastereoselectivity;

D O I：

10.1055/s-2006-926456

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An attractive intermediate in the total synthesis of the eleutherobin core has been obtained. Both syn and anti aldol diastereoisomers were synthesized by two different diastereoselective reaction sequences from 5-methyl-4-(pyrrolydin-1'-yl)-5H-furan-2-one. Each diastereoisomer was esterified and subjected to an intramolecular Diels-Alder reaction, which led to an intermediate that possesses rings A and C of the eleutherobin skeleton.

引用

页码：1673 / 1681

页数：9

共 34 条

[1]

AGARWAL SG, 1981, INDIAN J CHEM B, V20, P164

[2] Synthesis of novel simplified sarcodictyin/eleutherobin analogs with potent microtubule-stabilizing activity, using ring closing metathesis as the key-step [J].

Beumer, R ;

Bayón, P ;

Bugada, P ;

Ducki, S ;

Mongelli, N ;

Sirtori, FR ;

Telser, J ;

Gennari, C .

TETRAHEDRON, 2003, 59 (44) :8803-8820

[3] Intramolecular Diels-Alder strategy in a synthetic approach to the eleutherobin core [J].

Bruyère, H ;

Samaritani, S ;

Ballereau, S ;

Tomas, A ;

Royer, J .

SYNLETT, 2005, (09) :1421-1424

[4] Asymmetric synthesis of 5-(1-hydroxyalkyl)-5-methyl-5H-furan-2-ones [J].

Bruyère, H ;

Ballereau, S ;

Selkti, M ;

Royer, J .

TETRAHEDRON, 2003, 59 (31) :5879-5886

[5] Studies on the stereoselective synthesis of the marine antitumor agent eleutherobin [J].

Carter, R ;

Hodgetts, K ;

McKenna, J ;

Magnus, P ;

Wren, S .

TETRAHEDRON, 2000, 56 (26) :4367-4382

[6] Synthesis of novel, simplified, C-7 substituted eleutheside analogues with potent microtubule-stabilizing activity [J].

Castoldi, D ;

Caggiano, L ;

Bayón, P ;

Costa, AM ;

Cappella, P ;

Sharon, O ;

Gennari, C .

TETRAHEDRON, 2005, 61 (08) :2123-2139

[7] A formal total synthesis of eleutherobin through an unprecedented kinetically controlled ring-closing-metathesis reaction of a densely functionalized diene [J].

Castoldi, D ;

Caggiano, L ;

Panigada, L ;

Sharon, O ;

Costa, AM ;

Gennari, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :588-591

[8] Design, synthesis and cytotoxic studies on the simplified oxy analog of eleutherobin [J].

Chandrasekhar, S ;

Jagadeshwar, V ;

Narsihmulu, C ;

Sarangapani, M ;

Krishna, DR ;

Vidyasagar, J ;

Vijay, D ;

Sastry, GN .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (14) :3687-3689

[9] The total synthesis of eleutherobin [J].

Chen, XT ;

Bhattacharya, SK ;

Zhou, BS ;

Gutteridge, CE ;

Pettus, TRR ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6563-6579

[10] SARCODICTYIN-A AND SARCODICTYIN-B, NOVEL DITERPENOIDIC ALCOHOLS ESTERIFIED BY (E)-N(1)-METHYLUROCANIC ACID - ISOLATION FROM THE MEDITERRANEAN STOLONIFER SARCODICTYON-ROSEUM [J].

DAMBROSIO, M ;

GUERRIERO, A ;

PIETRA, F .

HELVETICA CHIMICA ACTA, 1987, 70 (08) :2019-2027

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