An approach to the total synthesis of welwistatin

被引：66

作者：

Greshock, Thomas J. ^{[1
]}

Funk, Raymond L. ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 12期

关键词：

D O I：

10.1021/ol0608799

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach to the total synthesis of the antimicrotubule agent welwistatin is described. Key transformations include (1) a 7-endo intramolecular conjugate addition reaction of enone 6 to deliver the strained bicyclo [4.3.1] decanone 5; (2) a 6 pi electrocyclic ring closure of trienecarbamate 16 followed by oxidation to afford protected aniline 17; and (3) an intramolecular cyclization of acetic acid derivative 18 to give rise to indole 19.

引用

页码：2643 / 2645

页数：3

共 31 条

[1] Synthetic studies on N-methylwelwitindolinone C isothiocyanate (welwistatin) and related substructures [J].

Avendaño, C ;

Menéndez, JC .

CURRENT ORGANIC SYNTHESIS, 2004, 1 (01) :65-82

[2] Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G [J].

Baran, PS ;

Richter, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15394-15396

[3] Rapid access to the welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones [J].

Baudoux, J ;

Blake, AJ ;

Simpkins, NS .

ORGANIC LETTERS, 2005, 7 (19) :4087-4089

[4] REACTIONS OF AMINES .14. AN OXIDATIVE REARRANGEMENT OF AMIDES [J].

BAUMGART.HE ;

STAKLIS, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (05) :1141-&

[5] REACTIONS OF AMINES .18. OXIDATIVE REARRANGEMENT OF AMIDES WITH LEAD-TETRAACETATE [J].

BAUMGARTEN, HE ;

SMITH, HL ;

STAKLIS, A .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (24) :3554-3561

[6] Aryllead(IV) reagents in synthesis:: Formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate [J].

Deng, HB ;

Konopelski, JP .

ORGANIC LETTERS, 2001, 3 (19) :3001-3004

[7]

FREDRICH P, 1988, TETRAHEDRON, V44, P1369

[8] A NEW HOMOGENEOUS PLATINUM-CONTAINING CATALYST FOR THE HYDROLYSIS OF NITRILES [J].

GHAFFAR, T ;

PARKINS, AW .

TETRAHEDRON LETTERS, 1995, 36 (47) :8657-8660

[9] The catalytic hydration of nitriles to amides using a homogeneous platinum phosphinito catalyst [J].

Ghaffar, T ;

Parkins, AW .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 160 (02) :249-261

[10] Synthesis of indoles via 6π-electrocyclic ring closures of trienecarbamates [J].

Greshock, TJ ;

Funk, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :4946-4947

← 1 2 3 4 →