An efficient, stereoselective synthesis of (-)-bulgecinine from (S)-aspartic acid

被引：14

作者：

Fehn, S ^{[1
]}

Burger, K ^{[1
]}

机构：

[1] UNIV LEIPZIG,DEPT ORGAN CHEM,D-04103 LEIPZIG,GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(97)00215-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A stereoselective synthesis of (2S,4S,5R)4-hydroxy-5-hydroxymethylproline 1 starting from (S)-aspartic acid 2 is described. The key step of the synthesis is the [Rh(OAc)(2)](2) catalyzed stereospecific transformation (de > 98%) of the hexafluoroacetone protected diazoketone 5 into the 4-oxoproline derivative 7. The keto function of 7 was reduced with high diastereoselectivity (de > 88%) to give the 4-cis-hydroxyproline derivative 8. After deprotection (-)-bulgecinine 1 was obtained from 9 on reduction of the ester moiety with LiBHEt3. (C) 1997 Elsevier Science Ltd.

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页码：2001 / 2005

页数：5

相关论文

共 27 条

[1] RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS [J].

ADAMS, J ;

SPERO, DM .

TETRAHEDRON, 1991, 47 (10-11) :1765-1808

[2] N-H insertion reactions of rhodium carbenoids .1. Preparation of alpha-amino acid and alpha-aminophosphonic acid derivatives [J].

Aller, E ;

Buck, RT ;

Drysdale, MJ ;

Ferris, L ;

Haigh, D ;

Moody, CJ ;

Pearson, ND ;

Sanghera, JB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (24) :2879-2884

[3] ELECTROCHEMICAL OXIDATION OF PROLINE DERIVATIVES - TOTAL SYNTHESES OF BULGECININE AND BULGECIN-C [J].

BARRETT, AGM ;

PILIPAUSKAS, D .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2787-2800

[4] TOTAL SYNTHESES OF BULGECININE AND BULGECIN-C FROM (2S,4R)-HYDROXYPROLINE [J].

BARRETT, AGM ;

PILIPAUSKAS, D .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) :5194-5196

[5] SYNTHESIS OF 2S,4S,5S-DIHYDROXYPIPECOLIC ACID AND BULGECININE [2S,4S,5R-4-HYDROXY-5-(HYDROXYMETHYL)PROLINE] FROM D-GLUCURONOLACTONE - A STRATEGY FOR THE SYNTHESIS OF 2S,4S-4-HYDROXY-ALPHA-AMINO ACIDS [J].

BASHYAL, BP ;

CHOW, HF ;

FLEET, GWJ .

TETRAHEDRON, 1987, 43 (02) :423-430

[6] ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2S,4S,5S-DIHYDROXYPIPECOLIC ACID, AND BULGECININE FROM DEUTERIUM-GLUCURONOLACTONE [J].

BASHYAL, BP ;

CHOW, HF ;

FLEET, GWJ .

TETRAHEDRON LETTERS, 1986, 27 (27) :3205-3208

[7]

BURGER K, 1992, SYNTHESIS-STUTTGART, P1150

[8] SYNTHESIS OF 4-OXO-L-PROLINE AND CIS-4-HYDROXY-L-PROLINE DERIVATIVES FROM L-ASPARTIC ACID [J].

BURGER, K ;

RUDOLPH, M ;

FEHN, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (02) :285-287

[9]

BURGER K, 1990, CHEM ZTG, V114, P249

[10]

BURGER K, 1993, ANGEW CHEM, V105, P293