Short and efficient synthesis of cadiolide B

被引：41

作者：

Boukouvalas, J ^{[1
]}

Pouliot, M ^{[1
]}

机构：

[1] Univ Laval, Dept Chim, Laval, PQ G1K 7P4, Canada

来源：

SYNLETT | 2005年 / 02期

关键词：

cross coupling; aldol reaction; 2-furanolates; lactones; total synthesis;

D O I：

10.1055/s-2004-837220

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of cadiolide B has been achieved in 6 steps and 42% overall yield from 4-bromo-2(5H)-furanone. The pathway involves sequential, regiocontrolled introduction of the three furanone substituents by means of aldol reactions and Suzuki cross coupling.

引用

收藏

页码：343 / 345

页数：3

相关论文

共 11 条

[1] Facile access to 4-aryl-2(5H)-furanones by Suzuki cross coupling:: Efficient synthesis of rubrolides C and E [J].

Boukouvalas, J ;

Lachance, N ;

Ouellet, M ;

Trudeau, M .

TETRAHEDRON LETTERS, 1998, 39 (42) :7665-7668

[2] Prunolides A, B, and C:: Novel tetraphenolic bis-spiroketals from the Australian ascidian Synoicum prunum [J].

Carroll, AR ;

Healy, PC ;

Quinn, RJ ;

Tranter, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2680-2682

[3]

JAS G, 1991, SYNTHESIS-STUTTGART, P965

[4] REGIOSELECTIVE ALDOL CONDENSATIONS OF BORON AND TIN FURANOLATES WITH ALDEHYDES - AN IMPROVED SYNTHESIS OF 2-(1'-HYDROXYALKYL)BUTENOLIDES [J].

JEFFORD, CW ;

JAGGI, D ;

BOUKOUVALAS, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (24) :1595-1596

[5]

Kotora M, 1997, SYNTHESIS-STUTTGART, P121

[6] RUBROLIDES-A-H, METABOLITES OF THE COLONIAL TUNICATE RITTERELLA-RUBRA [J].

MIAO, SC ;

ANDERSEN, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6275-6280

[7] New rubrolides from the ascidian Synoicum blochmanni [J].

Ortega, MJ ;

Zubía, E ;

Ocaña, JM ;

Naranjo, S ;

Salvá, J .

TETRAHEDRON, 2000, 56 (24) :3963-3967

[8] The discovery of rofecoxib, [MK 966, Vioxx®, 4-(4′-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2 inhibitor [J].

Prasit, P ;

Wang, Z ;

Brideau, C ;

Chan, CC ;

Charleson, S ;

Cromlish, W ;

Ethier, D ;

Evans, JF ;

Ford-Hutchinson, AW ;

Gauthier, JY ;

Gordon, R ;

Guay, J ;

Gresser, M ;

Kargman, S ;

Kennedy, B ;

Leblanc, Y ;

Léger, S ;

Mancini, J ;

O'Neill, GP ;

Ouellet, M ;

Percival, MD ;

Perrier, H ;

Riendeau, D ;

Rodger, I ;

Tagari, P ;

Thérien, M ;

Vickers, P ;

Wong, E ;

Xu, LJ ;

Young, RN ;

Zamboni, R ;

Boyce, S ;

Rupniak, N ;

Forrest, N ;

Visco, D ;

Patrick, D .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (13) :1773-1778

[9]

Ruel FS, 1998, ORG SYNTH, V75, P69

[10] Cadiolides A and B, new metabolites from an ascidian of the genus Botryllus [J].

Smith, CJ ;

Hettich, RL ;

Jompa, J ;

Tahir, A ;

Buchanan, MV ;

Ireland, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :4147-4150