Synthesis of cycloisodityrosine revisited: A selective ring forming process

被引：14

作者：

Bigot, A ^{[1
]}

Zhu, JP ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(97)10664-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cycloetherification of dipeptide (L,L) N-Boc-(4-fluoro-3-nitro)Phe-Dopa methyl ester (11) gave exclusively the (m,p)-cyclophane (14) at the expense of the 15-membered (p,p)cyclophane (16). An efficient synthesis of cycloisodityrosine was consequently developed (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：551 / 554

页数：4

共 26 条

[1] SNAR-BASED MACROCYCLIZATION - AN APPLICATION TO THE SYNTHESIS OF VANCOMYCIN FAMILY MODELS [J].

BEUGELMANS, R ;

SINGH, GP ;

BOISCHOUSSY, M ;

CHASTANET, J ;

ZHU, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5535-5542

[2] A formal total synthesis of deoxybouvardin [J].

Bigot, A ;

Beugelmans, R ;

Zhu, JP .

TETRAHEDRON, 1997, 53 (31) :10753-10764

[3]

BIGOT A, UNPUB

[4] Synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives [J].

Boger, DL ;

Zhou, JC ;

Borzilleri, RM ;

Nukui, S ;

Castle, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :2054-2069

[5] SELECTIVELY PROTECTED L-DOPA DERIVATIVES - APPLICATION OF THE BENZYLIC HYDROPEROXIDE REARRANGEMENT [J].

BOGER, DL ;

YOHANNES, D .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (23) :5283-5286

[6] INTRAMOLECULAR ULLMANN CONDENSATION REACTION - AN EFFECTIVE APPROACH TO MACROCYCLIC DIARYL ETHERS [J].

BOGER, DL ;

YOHANNES, D .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1763-1767

[7] Synthesis of the vancomycin CD and DE ring systems [J].

Boger, DL ;

Borzilleri, RM ;

Nukui, S ;

Beresis, RT .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4721-4736

[8] Synthesis of model tricyclic C-O-D-O-E-F-O-G ring of teicoplanin [J].

BoisChoussy, M ;

Vergne, C ;

Neuville, L ;

Beugelmans, R ;

Zhu, JP .

TETRAHEDRON LETTERS, 1997, 38 (33) :5795-5798

[9] Synthesis of modified carboxyl binding pockets of vancomycin and teicoplanin [J].

BoisChoussy, M ;

Neuville, L ;

Beugelmans, R ;

Zhu, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9309-9322

[10]

BORCHARDT A, 1995, SYNLETT, P539

← 1 2 3 →