Synthesis of the C9-C25 fragment of L-755,807. Evidence for the relative configuration of the side-chain.

被引：20

作者：

Clark, AJ ^{[1
]}

Ellard, JM ^{[1
]}

机构：

[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 33期

关键词：

stereochemistry; polyenes; natural products; coupling reactions;

D O I：

10.1016/S0040-4039(98)01190-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both diastereomers of the side-chain model (2) and C9-C25 fragment (3) of the B2 selective Bradykinin inhibitor L-755,807 have been prepared and their C-13 data compared to those of the natural product and those theoretically predicted by a combination of molecular mechanics and SOS-DFPT/IGLO calculations. The data suggest that the relative configuration of the C23 and C24 methyl groups is syn. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6033 / 6036

页数：4

共 9 条

[1] REACTION OF ORGANOBORANES WITH 2-BROMOACROLEIN . A FACILE 1-STAGE SYNTHESIS OF ALPHA-BROMO ALDEHYDES [J].

BROWN, HC ;

KABALKA, GW ;

RATHKE, MW ;

ROGIC, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (15) :4165-&

[2] CHEMISTRY OF OXAZIRIDINES .15. ASYMMETRIC OXIDATIONS USING 3-SUBSTITUTED 1,2-BENZISOTHIAZOLE 1,1-DIOXIDE OXIDES [J].

DAVIS, FA ;

THIMMAREDDY, R ;

MCCAULEY, JP ;

PRZESLAWSKI, RM ;

HARAKAL, ME ;

CARROLL, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :809-815

[3] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC IONOMYCIN [J].

EVANS, DA ;

DOW, RL ;

SHIH, TL ;

TAKACS, JM ;

ZAHLER, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5290-5313

[4]

Griffith W.P., 1990, Aldrichim Acta, V23, P13

[5] L-755,807, a new non-peptide bradykinin binding inhibitor from an endophytic Microsphaeropsis sp. [J].

Lam, YKT ;

Hensens, OD ;

Ransom, R ;

Giacobbe, RA ;

Polishook, J ;

Zink, D .

TETRAHEDRON, 1996, 52 (05) :1481-1486

[6] Assignment of relative configuration to acyclic compounds based on C-13 NMR shifts. A density functional and molecular mechanics study [J].

Stahl, M ;

Schopfer, U ;

Frenking, G ;

Hoffmann, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8083-8088

[7] STEREOSPECIFIC CROSS-COUPLING OF VINYL HALIDES WITH VINYL TIN REAGENTS CATALYZED BY PALLADIUM [J].

STILLE, JK ;

GROH, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :813-817

[8] SIMPLE AND SELECTIVE METHOD FOR RCHO-](E)-RCH=CHX CONVERSION BY MEANS OF A CHX3-CRCL2 SYSTEM [J].

TAKAI, K ;

NITTA, K ;

UTIMOTO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7408-7410

[9] SYNTHESIS OF THE ALIPHATIC DEPSIDE (+)-BOURGEANIC ACID [J].

WHITE, JD ;

JOHNSON, AT .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3347-3358

← 1 →