Stereoselective synthesis of unnatural aminoacids cis-4-hydroxyproline and bulgecinine

被引：27

作者：

Madau, A ^{[1
]}

Porzi, G ^{[1
]}

Sandri, S ^{[1
]}

机构：

[1] UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,I-40126 BOLOGNA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 03期

关键词：

D O I：

10.1016/0957-4166(96)00079-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new stereoselective synthesis of both (2R,4R)- and (2S,4S)-4-hydroxy-proline and (+)- and (-)-bulgecinine was performed starting from synthons 1 or 1', respectively, The synthetic route has been established via a novel assisted cleavage of a disubstituted amide in mild conditions and successive stereocontrolled iodocyclization (Schemes 1 and 2), (C) 1996 Elsevier Science Ltd

引用

页码：825 / 830

页数：6

共 10 条

[1]

ARCELLI A, IN PRESS TETRAHEDRON

[2] 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

[3]

DArrigo MC, 1995, J CHEM RES-S, P430

[4]

DARRIGO MC, 1995, J CHEM RES-S, P162

[5] AN EFFICIENT ROUTE TO 1,3-AMINO HYDROXYL SYSTEM VIA ELECTROPHILIC LACTONIZATION OF 2-AMINO-4-PENTENOIC ACID-DERIVATIVES - STEREOSELECTIVE SYNTHESIS OF (-)-BULGECININE [J].

OHFUNE, Y ;

HORI, K ;

SAKAITANI, M .

TETRAHEDRON LETTERS, 1986, 27 (50) :6079-6082

[6] DIASTEREOSELECTIVE ALKYLATION OF (3S)-3-METHYLPIPERAZINE-2,5-DIONE AND (3R)-3-METHYLPIPERAZINE-2,5-DIONE DERIVATIVES - A CONVENIENT APPROACH TO BOTH (S)-ALANINE AND (R)-ALANINE [J].

ORENA, M ;

PORZI, G ;

SANDRI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6532-6536

[7]

ORENA M, 1993, J CHEM RES-S, P318

[8] SYNTHESIS OF (3R, 6R)-3,6-DIALKYLPIPERAZIN-2,5-DIONE AND (3S, 6S)-3,6-DIALKYLPIPERAZIN-2,5-DIONE DERIVATIVES AS USEFUL INTERMEDIATES TO BOTH (R)-ALPHA-AMINO-ACID AND (S)-ALPHA-AMINO-ACIDS [J].

PORZI, G ;

SANDRI, S .

TETRAHEDRON-ASYMMETRY, 1994, 5 (03) :453-464

[9]

PORZI G, 1996, IN PRESS TETRAHEDRON

[10] SYNTHESIS OF BULGECININE - A NEW AMINO-ACID IN BULGECINS [J].

WAKAMIYA, T ;

YAMANOI, K ;

NISHIKAWA, M ;

SHIBA, T .

TETRAHEDRON LETTERS, 1985, 26 (39) :4759-4760

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