Preparation of hexahydrobenzo[f]isoquinolines using a vinylogous Pictet-Spengler cyclization

被引：19

作者：

Cesati, RR ^{[1
]}

Katzenellenbogen, JA ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 23期

关键词：

D O I：

10.1021/ol006533u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A vinylogous Pictet-Spengler cyclization has been carried out using activated aldehydes, ketones, and alkynes to prepare a variety of substituted hexahydrobenzo[f]isoquinolines. A unique set of conditions was utilized to effect efficient cyclization with acid sensitive electrophiles.

引用

收藏

页码：3635 / 3638

页数：4

相关论文

共 39 条

[1] A total asymmetric synthesis of (-)-suaveoline [J].

Bailey, PD ;

Morgan, KM .

CHEMICAL COMMUNICATIONS, 1996, (12) :1479-1480

[2] THE FORMATION OF OPTICALLY-ACTIVE 1,3-DISUBSTITUTED AND 1,1,3-TRISUBSTITUTED TETRAHYDRO-BETA-CARBOLINES USING A MODIFIED PICTET-SPENGLER REACTION [J].

BAILEY, PD ;

HOLLINSHEAD, SP ;

DAUTER, Z .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (21) :1507-1509

[3] DETERMINATION OF AN E-STRUCTURE OR A Z-STRUCTURE OF A SUBSTITUTED ALKENE BY C-13 NMR - CALCULATION OF THE CHEMICAL DISPLACEMENT OF ETHYLENIC CARBONS [J].

BARILLIER, D ;

STROBEL, MP ;

MORIN, L ;

PAQUER, D .

TETRAHEDRON, 1983, 39 (05) :767-775

[4] SELECTIVE FORMATION OF HETERODIMERIC BIS-BIDENTATE AMINOTHIOL-OXOMETAL COMPLEXES OF RHENIUM(V) [J].

CHI, DY ;

KATZENELLENBOGEN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7045-7046

[5] HOMODIMERIC AND HETERODIMERIC BIS(AMINO THIOL) OXOMETAL COMPLEXES WITH RHENIUM(V) AND TECHNETIUM(V) - CONTROL OF HETERODIMERIC COMPLEX-FORMATION AND AN APPROACH TO METAL-COMPLEXES THAT MIMIC STEROID-HORMONES [J].

CHI, DY ;

ONEIL, JP ;

ANDERSON, CJ ;

WELCH, MJ ;

KATZENELLENBOGEN, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (07) :928-937

[6] Enantioselective total synthesis of ecteinascidin 743 [J].

Corey, EJ ;

Gin, DY ;

Kania, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (38) :9202-9203

[7] Enantiospecific formation of trans 1,3-disubstituted tetrahydro-beta-carbolines by the Pictet-Spengler reaction and conversion of cis diastereomers into their trans counterparts by scission of the C-1/N-2 bond [J].

Cox, ED ;

Hamaker, LK ;

Li, J ;

Yu, P ;

Czerwinski, KM ;

Deng, L ;

Bennett, DW ;

Cook, JM ;

Watson, WH ;

Krawiec, M .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (01) :44-61

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

COX, ED ;

COOK, JM .

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

[9] Pictet-Spengler reaction of biogenic amines with (2R)-N-glyoxyloylbornane-10,2-sultam.: Enantioselective synthesis of (S)-(+)-N-methylcalycotomine and (R)-(+)-xylopinine [J].

Czarnocki, Z ;

Arazny, Z .

HETEROCYCLES, 1999, 51 (12) :2871-2879

[10] BETA-KETO-DELTA-VALEROLACTONE - SYNTHESIS AND USE AS METHYLVINYLKETONE ANION EQUIVALENT IN MICHAEL ADDITIONS [J].

DANGELO, J ;

GOMEZPARDO, D .

TETRAHEDRON LETTERS, 1991, 32 (26) :3063-3066

← 1 2 3 4 →