Rhodium-carbenoid-mediated intermolecular O-H insertion reactions: a dramatic additive effect. Application in the synthesis of an ascomycin derivative

被引：42

作者：

Nelson, TD ^{[1
]}

Song, ZJ ^{[1
]}

Thompson, AS ^{[1
]}

Zhao, MZ ^{[1
]}

DeMarco, A ^{[1
]}

Reamer, RA ^{[1
]}

Huntington, MF ^{[1
]}

Grabowski, EJJ ^{[1
]}

Reider, PJ ^{[1
]}

机构：

[1] Merck Res Labs, Dept Proc Chem, Rahway, NJ 07065 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(00)00069-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalyst system of Rh-2(oct)(4)/DIPEA or TMU allows for the rapid construction of alpha-alkoxyketones from the corresponding alpha-diazo ketone and alcohol. This methodology was applied to the synthesis of immunoregulant 1. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1877 / 1881

页数：5

相关论文

共 16 条

[1] Potent immunosuppressive C32-O-arylethyl ether derivatives of ascomycin with reduced toxicity. [J].

Armstrong, HM ;

Wong, F ;

Holmes, MA ;

Sinclair, PJ ;

Goulet, MT ;

Dumont, FJ ;

Staruch, M ;

Koprak, S ;

Peterson, LB ;

Rosa, R ;

Wilusz, MB ;

Wiederrecht, GJ ;

Cryan, JG ;

Wyvratt, MJ ;

Parsons, WH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (14) :2089-2094

[2] A MILD PROCEDURE FOR ETHERIFICATION OF ALCOHOLS WITH PRIMARY ALKYL-HALIDES IN THE PRESENCE OF SILVER TRIFLATE [J].

BURK, RM ;

GAC, TS ;

ROOF, MB .

TETRAHEDRON LETTERS, 1994, 35 (44) :8111-8112

[3]

BYRNE KM, 1992, MICROBIAL METABOLITE, V32, P29

[4] EFFECTS OF TRIETHYLAMINE IN ASYMMETRIC REDUCTION USING OXAZABOROLIDINE REAGENTS [J].

CAI, DW ;

TSCHAEN, D ;

SHI, YJ ;

VERHOEVEN, TR ;

REAMER, RA ;

DOUGLAS, AW .

TETRAHEDRON LETTERS, 1993, 34 (20) :3243-3246

[5] RHODIUM-CARBENOID MEDIATED O-H INSERTION REACTIONS - O-H INSERTION VS H-ABSTRACTION AND EFFECT OF CATALYST [J].

COX, GG ;

MILLER, DJ ;

MOODY, CJ ;

SIE, ERHB ;

KULAGOWSKI, JJ .

TETRAHEDRON, 1994, 50 (10) :3195-3212

[6] DIRHODIUM(II) TETRAKIS(CARBOXAMIDATES) WITH CHIRAL LIGANDS - STRUCTURE AND SELECTIVITY IN CATALYTIC METAL CARBENE TRANSFORMATIONS [J].

DOYLE, MP ;

WINCHESTER, WR ;

HOORN, JAA ;

LYNCH, V ;

SIMONSEN, SH ;

GHOSH, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :9968-9978

[7]

Goulet Mark T., 1994, Perspectives in Drug Discovery and Design, V2, P145, DOI 10.1007/BF02171741

[8] ALKYL ETHER ANALOGS OF THE FK-506 RELATED, IMMUNOSUPPRESSIVE MACROLIDE L-683,590 (ASCOMYCIN) [J].

GOULET, MT ;

HODKEY, DW ;

STARUCH, MJ ;

DUMONT, FJ ;

CRYAN, JG ;

PARSONS, WH ;

WYVRATT, MJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (07) :921-926

[9] RHODIUM CARBENOID O-H INSERTION REACTIONS WITH PHENOLS - A FACILE METHOD FOR THE SYNTHESIS OF TRIALKYL 2-ARYLOXYPHOSPHONOACETATES AND THEIR USE IN THE PREPARATION OF 2-ARYLOXY-3-PHENYLPROPANOATES [J].

HAIGH, D .

TETRAHEDRON, 1994, 50 (10) :3177-3194

[10]

HAUPTMANN S, 1969, J PRAKT CHEM, P604