Chiral auxiliary mediated Pictet-Spengler reactions - Asymmetric syntheses of (-)-laudanosine, (+)-glaucine and (-)-xylopinine.

被引：63

作者：

Comins, DL

Thakker, PM

Baevsky, MF

Badawi, MM

机构：

来源：

TETRAHEDRON | 1997年 / 53卷 / 48期

关键词：

D O I：

10.1016/S0040-4020(97)01018-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclohexyl-based chiral auxiliaries can be used effectively in an asymmetric Pictet-Spengler synthesis of tetrahydroisoquinoline, aporphine and protoberbine alkaloids. Using this strategy, concise asymmetric syntheses of (-)-laudanosine, (+)-glaucine and (+)-xylopinine have been accomplished. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：16327 / 16340

页数：14

相关论文

共 33 条

[1]

[Anonymous], 1996, Adv. Nitrogen Heterocycl

[2]

BOHLMANN C, 1985, LIEBIGS ANN CHEM, P1752

[3] Anionic cyclizations of chiral 2,3-dihydro-4-pyridones: A five-step, asymmetric synthesis of indolizidine 209D [J].

Comins, DL ;

Zhang, YM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (48) :12248-12249

[4] ASYMMETRIC PICTET-SPENGLER SYNTHESIS OF TETRAHYDROISOQUINOLINES - AN ENANTIOSELECTIVE SYNTHESIS OF (-)-LAUDANOSINE [J].

COMINS, DL ;

BADAWI, MM .

TETRAHEDRON LETTERS, 1991, 32 (26) :2995-2996

[5] Asymmetric addition of Grignard reagents to chiral 1-acylpyridinium salts: A chiral auxiliary study [J].

Comins, DL ;

GuerraWeltzien, L .

TETRAHEDRON LETTERS, 1996, 37 (22) :3807-3810

[6] EFFICIENT SYNTHESIS AND RESOLUTION OF TRANS-2-(1-ARYL-1-METHYLETHYL)CYCLOHEXANOLS - PRACTICAL ALTERNATIVES TO 8-PHENYLMENTHOL [J].

COMINS, DL ;

SALVADOR, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4656-4661

[7] ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS [J].

COMINS, DL ;

JOSEPH, SP ;

GOEHRING, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (11) :4719-4728

[8] Regio- and stereoselective intramolecular Heck reactions of N-acyl-2,3-dihydro-4-pyridones [J].

Comins, DL ;

Joseph, SP ;

Zhang, YM .

TETRAHEDRON LETTERS, 1996, 37 (06) :793-796

[9] AN EFFICIENT PREPARATION OF (+)-TRANS-2-(ALPHA-CUMYL)CYCLOHEXANOL ((+)-TCC) - A PRACTICAL ALTERNATIVE TO (+)-8-PHENYLMENTHOL [J].

COMINS, DL ;

SALVADOR, JM .

TETRAHEDRON LETTERS, 1993, 34 (05) :801-804

[10] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

← 1 2 3 4 →