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
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
收藏
页码:1398 / 1400
页数:3
相关论文
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 [J].
Ahmad, Nadia M. ;
Rodeschini, Vincent ;
Simpkins, Nigel S. ;
Ward, Simon E. ;
Blake, Alexander J. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) :4803-4815
[2]   Synthetic studies on N-methylwelwitindolinone C isothiocyanate (welwistatin) and related substructures [J].
Avendaño, C ;
Menéndez, JC .
CURRENT ORGANIC SYNTHESIS, 2004, 1 (01) :65-82
[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]   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
[5]   Diastereoselectivity in the formation of quaternary centers with aryllead(IV) tricarboxylates [J].
Elliott, GI ;
Konopelski, JP ;
Olmstead, MM .
ORGANIC LETTERS, 1999, 1 (11) :1867-1870
[6]   Bridgehead enolates: Substitution and asymmetric desymmetrization of small bridged carbonyl compounds by lithium amide bases [J].
Giblin, GMP ;
Kirk, DT ;
Mitchell, L ;
Simpkins, NS .
ORGANIC LETTERS, 2003, 5 (10) :1673-1675
[7]   An approach to the total synthesis of welwistatin [J].
Greshock, Thomas J. ;
Funk, Raymond L. .
ORGANIC LETTERS, 2006, 8 (12) :2643-2645
[8]   REMOTE DOUBLE-BOND MIGRATION VIA RHODIUM CATALYSIS - NOVEL ENONE TRANSPOSITION [J].
GRIECO, PA ;
NISHIZAWA, M ;
MARINOVIC, N ;
EHMANN, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (22) :7102-7104
[9]   Oxidized welwitindolinones from terrestrial Fischerella spp. [J].
Jimenez, JI ;
Huber, U ;
Moore, RE ;
Patterson, GML .
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 [J].
Jung, ME ;
Slowinski, F .
TETRAHEDRON LETTERS, 2001, 42 (39) :6835-6838