Towards a total synthesis of the manadomanzamine alkaloids: the first asymmetric construction of the pentacyclic indole core

被引：19

作者：

Allin, Steven M. ^{[1
]}

Duffy, Liam J.

Bulman Page, Philip C.

McKee, Vickie

McKenzie, Michael J.

机构：

[1] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England

[2] Charnwood Mol Ltd, Loughborough LE11 5GA, Leics, England

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 27期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2007.05.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a highly diastereoselective approach for the synthesis of the pentacyclic indole core of the manadomanzamine alkaloid skeleton, with complete control over the relative and absolute stereochemistries at the three contiguous stereocentres at ring positions 1, 10, and 24, from a readily available chiral template. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.

引用

页码：4711 / 4714

页数：4

共 20 条

[1] Complementary stereoselective conjugate addition reactions on indolo[2,3-α]-quinolizine templates [J].

Allin, SM ;

Khera, JS ;

Thomas, CI ;

Witherington, J ;

Doyle, K ;

Elsegood, MRJ ;

Edgar, M .

TETRAHEDRON LETTERS, 2006, 47 (12) :1961-1964

[2] A highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to natural product synthesis [J].

Allin, SM ;

Thomas, CI ;

Allard, JE ;

Doyle, K ;

Elsegood, MRJ .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (19) :4179-4186

[3] An asymmetric synthesis of both enantiomers of the indole alkaloid deplancheine [J].

Allin, SM ;

Thomas, CI ;

Doyle, K ;

Elsegood, MRJ .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :357-359

[4] Highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to indole natural product synthesis [J].

Allin, SM ;

Thomas, CI ;

Allard, JE ;

Doyle, K ;

Elsegood, MRJ .

TETRAHEDRON LETTERS, 2004, 45 (38) :7103-7105

[5] A formal asyrnmetric synthesis of both enantiomers of the Erythrina alkaloid 3-demethoxyerythratidinone [J].

Allin, SM ;

Streetley, GB ;

Slater, M ;

James, SL ;

Martin, WP .

TETRAHEDRON LETTERS, 2004, 45 (28) :5493-5496

[6] Facile and highly stereoselective synthesis of the tetracyclic erythrinane core [J].

Allin, SM ;

James, SL ;

Elsegood, MRJ ;

William, PM .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) :9464-9467

[7] Stereoselective synthesis of the indolizinoindole ring system [J].

Allin, SM ;

Thomas, CI ;

Allard, JE ;

Duncton, M ;

Elsegood, MRJ ;

Edgar, M .

TETRAHEDRON LETTERS, 2003, 44 (11) :2335-2337

[8] Stereoselective synthesis of isoquinoline derivatives from bicyclic lactam templates [J].

Allin, SM ;

Vaidya, DG ;

James, SL ;

Allard, JE ;

Smith, TAD ;

McKee, V ;

Martin, WP .

TETRAHEDRON LETTERS, 2002, 43 (20) :3661-3663

[9] Stereoselective synthesis of the pyrroloisoquinoline ring system [J].

Allin, SM ;

James, SL ;

Martin, WP ;

Smith, TAD ;

Elsegood, MRJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (22) :3029-3036

[10] Stereoselective synthesis of the pyrroloisoquinoline ring system [J].

Allin, SM ;

James, SL ;

Martin, WP ;

Smith, TAD .

TETRAHEDRON LETTERS, 2001, 42 (23) :3943-3946

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