A case of Pictet-Spengler revisited: Application to the synthesis of dihydroisocoumarins

被引：6

作者：

Choukchou-Braham, N ^{[1
]}

Mostefa-Kara, B

Cheikh, N

Didi, MA

Villemin, D

机构：

[1] Univ Abou Bekr, Fac Sci, Dept Chim, Lab Catalyse & Synth Chim Organ, Tilimsen, Algeria

[2] Univ Caen, ENSICAEN, UMR 6507, Caen, France

来源：

SYNTHETIC COMMUNICATIONS | 2005年 / 35卷 / 02期

关键词：

dihydroisocoumarins; benzylic alcohol; Pictet-Spengler reaction;

D O I：

10.1081/SCC-200048399

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of Pictet-Spengler was revisited, and its modified conditions were applied to develop a general methodology toward the synthesis of dihydroisocoumarins containing a no-electron rich aromatic ring.

引用

页码：169 / 178

页数：10

共 23 条

[1]

ARNOLDI A, 1992, GAZZ CHIM ITAL, V122, P403

[2] PHEROMONES .86. 3,4-DIHYDROISOCOUMARINS, A NEW CLASS OF ANT TRAIL PHEROMONES [J].

BESTMANN, HJ ;

KERN, F ;

SCHAFER, D ;

WITSCHEL, MC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (06) :795-796

[3]

BHIDE BH, 1992, INDIAN J CHEM B, V31, P43

[4] THE CHEMISTRY OF FUNGI .5. THE CONSTITUTION OF CITRININ [J].

BROWN, JP ;

ROBERTSON, A ;

WHALLEY, WB ;

CARTWRIGHT, NJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1949, (APR) :867-879

[5]

Bruynzell D. P., 1987, CONTACT DERMATITIS, P181

[6]

BRUYNZELL DP, 1986, CONTACT DERMATITIS, P128

[7] ISOLATION, STRUCTURE DETERMINATION AND SYNTHESIS OF NEW DIHYDROISOCOUMARINS FROM GINKGO-BILOBA L [J].

CHOUKCHOUBRAHAM, N ;

ASAKAWA, Y ;

LEPOITTEVIN, JP .

TETRAHEDRON LETTERS, 1994, 35 (23) :3949-3952

[8] ENANTIOSELECTIVE SYNTHESIS OF MONOCERIN AND FUSARENTIN ETHERS - ANTIFUNGAL AND INSECTICIDAL FUNGAL METABOLITES [J].

DILLON, MP ;

SIMPSON, TJ ;

SWEENEY, JB .

TETRAHEDRON LETTERS, 1992, 33 (49) :7569-7572

[9] REACTION OF SERINE PROTEASES WITH SUBSTITUTED ISOCOUMARINS - DISCOVERY OF 3,4-DICHLOROISOCOUMARIN, A NEW GENERAL MECHANISM BASED SERINE PROTEASE INHIBITOR [J].

HARPER, JW ;

HEMMI, K ;

POWERS, JC .

BIOCHEMISTRY, 1985, 24 (08) :1831-1841

[10]

Hausen B. M., 1990, CONTACT DERMATITIS, P59

← 1 2 3 →