Bridgehead enolates and bridgehead alkenes in a welwistatin model series

被引：22

作者：

Boissel, Valerie ^{[2
]}

Simpkins, Nigel S. ^{[2
]}

Bhalay, Gurdip ^{[1
]}

Blake, Alexander J. ^{[2
]}

Lewis, William ^{[2
]}

机构：

[1] Horsham Res Ctr, Novartis Inst Biomed Res, Global Discovery Chem, Horsham, W Sussex, England

[2] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

CHEMICAL COMMUNICATIONS | 2009年 / 11期

关键词：

SKELETON; WELWITINDOLINONES; CLUSIANONE; EFFICIENT;

D O I：

10.1039/b820674k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bridgehead metallation is possible in a ketone having the welwistatin skeleton, and this facilitates installation of the isothiocyanate function present in the natural product, and also enables synthesis of remarkable bridgehead alkenes.

引用

页码：1398 / 1400

页数：3

共 23 条

[1] Synthesis of polyprenylated acylphloroglucinols using bridgehead lithiation: The total synthesis of racemic clusianone and a formal synthesis of racemic garsubellin A
Ahmad, Nadia M.
Rodeschini, Vincent
Simpkins, Nigel S.
Ward, Simon E.
Blake, Alexander J.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) : 4803 - 4815
[2] Synthetic studies on N-methylwelwitindolinone C isothiocyanate (welwistatin) and related substructures
Avendaño, C
Menéndez, JC
[J]. CURRENT ORGANIC SYNTHESIS, 2004, 1 (01) : 65 - 82
[3] Rapid access to the welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones
Baudoux, J
Blake, AJ
Simpkins, NS
[J]. ORGANIC LETTERS, 2005, 7 (19) : 4087 - 4089
[4] Aryllead(IV) reagents in synthesis:: Formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate
Deng, HB
Konopelski, JP
[J]. ORGANIC LETTERS, 2001, 3 (19) : 3001 - 3004
[5] Diastereoselectivity in the formation of quaternary centers with aryllead(IV) tricarboxylates
Elliott, GI
Konopelski, JP
Olmstead, MM
[J]. ORGANIC LETTERS, 1999, 1 (11) : 1867 - 1870
[6] Bridgehead enolates: Substitution and asymmetric desymmetrization of small bridged carbonyl compounds by lithium amide bases
Giblin, GMP
Kirk, DT
Mitchell, L
Simpkins, NS
[J]. ORGANIC LETTERS, 2003, 5 (10) : 1673 - 1675
[7] An approach to the total synthesis of welwistatin
Greshock, Thomas J.
Funk, Raymond L.
[J]. ORGANIC LETTERS, 2006, 8 (12) : 2643 - 2645
[8] REMOTE DOUBLE-BOND MIGRATION VIA RHODIUM CATALYSIS - NOVEL ENONE TRANSPOSITION
GRIECO, PA
NISHIZAWA, M
MARINOVIC, N
EHMANN, WJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (22) : 7102 - 7104
[9] Oxidized welwitindolinones from terrestrial Fischerella spp.
Jimenez, JI
Huber, U
Moore, RE
Patterson, GML
[J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (04): : 569 - 572
[10] Rhodium-catalyzed decomposition of indole-substituted α-diazo-β-keto esters:: three different reactions based on indole oxidation state
Jung, ME
Slowinski, F
[J]. TETRAHEDRON LETTERS, 2001, 42 (39) : 6835 - 6838

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