Construction of spirolactones with concomitant formation of the fused quaternary centre - application to the synthesis of natural products

被引：109

作者：

Bartoli, Alexandra ^{[1
]}

Rodier, Fabien ^{[1
]}

Commeiras, Laurent ^{[1
]}

Parrain, Jean-Luc ^{[1
]}

Chouraqui, Gaelle ^{[1
]}

机构：

[1] Aix Marseille Univ, Inst Sci Mol Marseille iSm2, UMR CNRS 6263, F-13397 Marseille 20, France

来源：

NATURAL PRODUCT REPORTS | 2011年 / 28卷 / 04期

关键词：

NEUTRAL SPHINGOMYELINASE INHIBITOR; VINYLOGOUS MANNICH REACTIONS; FREE-RADICAL REACTIONS; SPIRO-GAMMA-LACTONES; PSEUDOARACHNIOTUS-ROSEUS; HETEROCYCLE SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; RUGULOVASINE-A; DIMETHYL ACETYLENEDICARBOXYLATE;

D O I：

10.1039/c0np00053a

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Polycyclic structures fused at a central carbon are of great interest due to their appealing conformational features and their structural implications in biological systems. Although progress in the development of synthetic methodologies towards such structures has been impressive, the stereoselective construction of such quaternary stereocentres remains a significant challenge in the total synthesis of natural products. This review highlights the progress in the formation of 1-oxaspiro[4.n]alkan-2-ones (2 <= n <= 7) with concomitant formation of the quaternary spiro centre.

引用

页码：763 / 782

页数：20

共 163 条

[21] DIASTEREOSELECTIVE SPIROANNELATION [J].

CANONNE, P ;

BOULANGER, R ;

BERNATCHEZ, M .

TETRAHEDRON LETTERS, 1987, 28 (42) :4997-5000

[22] A NOVEL SYNTHESIS OF UNSATURATED SPIRO COMPOUNDS BASED ON REACTIONS OF BIFUNCTIONAL ORGANOMETALLIC REAGENTS [J].

CANONNE, P ;

BOULANGER, R ;

ANGERS, P .

TETRAHEDRON LETTERS, 1991, 32 (42) :5861-5864

[23] Levistolide A overcomes P-glycoprotein-mediated drug resistance in human breast carcinoma cells [J].

Chen, Fei ;

Wang, Tao ;

Wang, Jia ;

Wang, Zi-qiang ;

Qian, Ming .

ACTA PHARMACOLOGICA SINICA, 2008, 29 (04) :458-464

[24] Indium-promoted preparation of substituted α-methylene-γ-lactones from 2-(bromomethyl)acrylic acid and carbonyl compounds [J].

Choudhury, PK ;

Foubelo, F ;

Yus, M .

TETRAHEDRON LETTERS, 1998, 39 (21) :3581-3584

[25] Stereoselective construction of quaternary stereocenters [J].

Christoffers, J ;

Baro, A .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1473-1482

[26] Synthesis and antiapoptotic activity of a novel analogue of the neutral sphingomyelinase inhibitor scyphostatin [J].

Claus, RA ;

Wüstholz, A ;

Müller, S ;

Bockmeyer, CL ;

Riedel, NH ;

Kinscherf, R ;

Deigner, HP .

CHEMBIOCHEM, 2005, 6 (04) :726-737

[27]

COLE RJ, 1976, TETRAHEDRON LETT, P3849

[28] OXIDATIVE CLEAVAGE OF AMIDES - A METHOD FOR SELECTIVE CHEMICAL DEGRADATION OF PEPTIDES [J].

COREY, EJ ;

HAEFELE, LF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (09) :2225-2228

[29] Formal synthesis of Abyssomicin C [J].

Couladouros, Elias A. ;

Bouzas, Emmanuel A. ;

Magos, Alexandros D. .

TETRAHEDRON, 2006, 62 (22) :5272-5279

[30] SPIRODIENONES-IV1 THE SYNTHESIS OF N-SULFONYLCYCLOHEXADIENIMINES AND RELATED DIENONES [J].

COUTTS, IGC ;

EDWARDS, M ;

MUSTO, DR ;

RICHARDS, DJ .

TETRAHEDRON LETTERS, 1980, 21 (52) :5055-5056

← 1 2 3 4 5 6 7 8 9 10 →