TIN(IV)-CATALYZED LACTONIZATION OF OMEGA-HYDROXY TRIFLUOROETHYL ESTERS

被引：16

作者：

WHITE, JD

GREEN, NJ

FLEMING, FF

机构：

[1] Department of Chemistry, Oregon State University, Corvallis

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 22期

关键词：

MACROLACTONIZATION; TRI-N-BUTYLMETHOXYSTANNANE;

D O I：

10.1016/S0040-4039(00)73624-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,1,1-Trifluoroethyl esters of omega-hydroxycarboxylic acids were prepared and their conversion to macrocyclic lactones, including ricinelaidic lactone, was studied in the presence of catalytic quantities of tin(IV) reagents; a mechanism involving exchange of alkoxytrialkyltin species is proposed.

引用

页码：3515 / 3518

页数：4

共 10 条

[1] SYNTHESIS OF MACROCYCLIC LACTONES - APPROACHES TO COMPLEX MACROLIDE ANTIBIOTICS
BACK, TG
[J]. TETRAHEDRON, 1977, 33 (23) : 3041 - 3059
[2] BLOODWORTH AJ, 1971, ORGANOTIN COMPOUNDS, V1, P168
[3] GENERAL, SELECTIVE SYNTHESIS OF THIOL ESTERS
MASAMUNE, S
KAMATA, S
DIAKUR, J
SUGIHARA, Y
BATES, GS
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (23): : 3693 - 3695
[4] RECENT DEVELOPMENTS IN THE TOTAL SYNTHESIS OF MACROLIDE ANTIBIOTICS
PATERSON, I
MANSURI, MM
[J]. TETRAHEDRON, 1985, 41 (18) : 3569 - 3624
[5] PEREYRE M, 1987, TIN ORGANIS SYNTHESI, P263
[6] POMMIER JC, 1967, TETRAHEDRON LETT, P5289
[7] REAGENTS FOR ORGANIC-SYNTHESIS - USE OF ORGANOSTANNYL OXIDES AS CATALYTIC NEUTRAL ESTERIFICATION AGENTS IN THE PREPARATION OF MACROLIDES
STELIOU, K
SZCZYGIELSKANOWOSIELSKA, A
FAVRE, A
POUPART, MA
HANESSIAN, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (25) : 7578 - 7579
[8] TIN-MEDIATED ESTERIFICATION IN MACROLIDE SYNTHESIS
STELIOU, K
POUPART, MA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (24) : 7130 - 7138
[9] Thalmann A., 1990, ORG SYNTH, V7, P470
[10] VALADE J, 1962, CR HEBD ACAD SCI, V254, P3693

← 1 →