SILOXANES - VERSATILE TEMPLATES FOR ACYCLIC STEREOCONTROL - SYNTHESIS OF THE C27-C33 SEGMENT OF RAPAMYCIN

被引：69

作者：

HALE, MR ^{[1
]}

HOVEYDA, AH ^{[1
]}

机构：

[1] BOSTON COLL,DEPT CHEM,CHESTNUT HILL,MA 02167

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 06期

关键词：

D O I：

10.1021/jo00032a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Five-membered siloxane rings may be employed to relay asymmetry along an acyclic chain in an efficient manner. Application of this method to the synthesis of the C27-C33 segment of the immunosuppressant rapamycin is reported.

引用

页码：1643 / 1645

页数：3

共 31 条

[1] SUBSTRATE-SPECIFICITY FOR THE HUMAN ROTAMASE FKBP - A VIEW OF FK506 AND RAPAMYCIN AS LEUCINE (TWISTED AMIDE) PROLINE MIMICS [J].

ALBERS, MW ;

WALSH, CT ;

SCHREIBER, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) :4984-4986

[2] PROBING IMMUNOSUPPRESSANT ACTION WITH A NONNATURAL IMMUNOPHILIN LIGAND [J].

BIERER, BE ;

SOMERS, PK ;

WANDLESS, TJ ;

BURAKOFF, SJ ;

SCHREIBER, SL .

SCIENCE, 1990, 250 (4980) :556-559

[3] ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].

CHA, JK ;

CHRIST, WJ ;

KISHI, Y .

TETRAHEDRON, 1984, 40 (12) :2247-2255

[4] ON STEREOCHEMISTRY OF OSMIUM-TETROXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].

CHA, JK ;

CHRIST, WJ ;

KISHI, Y .

TETRAHEDRON LETTERS, 1983, 24 (37) :3943-3946

[5] STEREOSELECTIVE OSMYLATION OF 1,1-DISUBSTITUTED OLEFINS - EFFECT OF ALLYLIC SUBSTITUENTS ON REACTION DIASTEREOSELECTIVITY [J].

EVANS, DA ;

KALDOR, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1698-1700

[6] ON THE CHEMISTRY AND HIGH-FIELD NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF RAPAMYCIN [J].

FINDLAY, JA ;

RADICS, L .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (06) :579-590

[7] SYNTHETIC STUDIES TOWARD RAPAMYCIN - A SOLUTION TO A PROBLEM IN CHIRALITY MERGER THROUGH USE OF THE IRELAND REACTION [J].

FISHER, MJ ;

MYERS, CD ;

JOGLAR, J ;

CHEN, SH ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5826-5834

[8]

FISHER MJ, 1991, J ORG CHEM, V56, P5834

[9] RAPAMYCIN AND FK506 BINDING-PROTEINS (IMMUNOPHILINS) [J].

FRETZ, H ;

ALBERS, MW ;

GALAT, A ;

STANDAERT, RF ;

LANE, WS ;

BURAKOFF, SJ ;

BIERER, BE ;

SCHREIBER, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1409-1411

[10]

GOULET MT, 1990, TETRAHEDRON LETT, V31, P4845

← 1 2 3 4 →