Asymmetric synthesis of (R)-(+)- and (S)-(-)-2,3-methylenedioxy-8-oxoberbine (gusanlung D)

被引：27

作者：

Chrzanowska, M ^{[1
]}

Dreas, A ^{[1
]}

Rozwadowska, MD ^{[1
]}

机构：

[1] Adam Mickiewicz Univ Poznan, Fac Chem, PL-60780 Poznan, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 07期

关键词：

D O I：

10.1016/j.tetasy.2004.02.017

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reaction of 6,7-methylenedioxy-3,4-dihydroisoquinoline with laterally lithiated o-toluamides in which the amine part derived from (1S,2S)-thiomicamine or (1R,2S)-2-amino-1-phenylpropanol, affording (R)-(+)- and (S)-(-)-2,3-methylenedioxy-8-oxoberbine in 77% and 64% yield, respectively, and with enantiomeric excess >99% is described. Physical and spectral data of the synthetic product differ from those reported for the natural alkaloid, gusanhang D. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1113 / 1120

页数：8

共 22 条

[1]

[Anonymous], [No title captured]

[2] Transformation of (+)-thiomicamine into a new ligand for the enantioselective addition of methyllithium to prochiral imines [J].

Brózda, D ;

Chrzanowska, M ;

Gluszynska, A ;

Rozwadowska, MD .

TETRAHEDRON-ASYMMETRY, 1999, 10 (24) :4791-4796

[3]

BROZDA D, 2001, ANN POLISH CHEM SOC, P264

[4] Enantioselective addition of organometallic compounds to 3,4-dihydroisoquinoline in the presence of oxazoline derivatives:: synthesis of (R)-(+)- and (S)-(-)-salsolidine [J].

Chrzanowska, M .

TETRAHEDRON-ASYMMETRY, 2002, 13 (22) :2497-2500

[5] SYNTHESIS OF ISOQUINOLINE ALKALOIDS - TOTAL SYNTHESIS OF (+/-)-STYLOPINE [J].

CHRZANOWSKA, M .

JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (03) :401-407

[6]

CHRZANOWSKA M, BOS 2002 INT C ORG S

[7] Asymmetric synthesis of the protoberberine alkaloid (S)-(-)-xylopinine using enantiopure sulfinimines [J].

Davis, FA ;

Mohanty, PK .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1290-1296

[8] Enantioselective modification of the Pomeranz-Fritsch-Bobbitt synthesis of tetrahydroisoquinoline alkaloids: synthesis of (-)-salsolidine and (-)-carnegine [J].

Gluszynska, A ;

Rozwadowska, MD .

TETRAHEDRON-ASYMMETRY, 2000, 11 (11) :2359-2366

[9] FACILE GENERATION AND TRAPPING OF ALPHA-OXO-O-QUINODIMETHANES - SYNTHESIS OF 3-ARYL-3,4-DIHYDROISOCOUMARINS AND PROTOBERBERINES [J].

KESSAR, SV ;

SINGH, P ;

VOHRA, R ;

KAUR, NP ;

VENUGOPAL, D .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6716-6720

[10]

Liu LG, 2003, SYNTHESIS-STUTTGART, P1705

← 1 2 3 →