Unified synthesis of eudesmanolides, combining biomimetic strategies with homogeneous catalysis and free-radical chemistry

被引：118

作者：

Barrero, AF ^{[1
]}

Rosales, A ^{[1
]}

Cuerva, JM ^{[1
]}

Oltra, JE ^{[1
]}

机构：

[1] Univ Granada, Fac Sci, Dept Organ Chem, E-18071 Granada, Spain

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 11期

关键词：

D O I：

10.1021/ol034510k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] A general procedure for the synthesis of both 12,6- and 12,8-eudesmanolides has been developed. The key step is the titanocene-catalyzed radical cyclization of accessible epoxygermacrolides. The novel reagent 2,4,6-trimethyl-1-trimethylsilyipyridinium chloride, both compatible with oxiranes and capable of regenerating Cp2TiCl2 from Cp2Ti(Cl)H and Cp2Ti(Cl)OAc, played an important role in the catalytic cycle leading to exocyclic alkenes.

引用

页码：1935 / 1938

页数：4

共 50 条

[21] WILLIAMS,GH - ADVANCES IN FREE-RADICAL CHEMISTRY
不详
PRODUCTS ET PROBLEMS PHARMACEUTIQUES, 1967, 22 (02): : 77 - &
[22] WILLIAMS,GH - ADVANCES IN FREE-RADICAL CHEMISTRY
SCHOFIEL.K
CHEMISTRY & INDUSTRY, 1967, (26) : 1135 - &
[23] THE CHEMISTRY BIOCHEMISTRY INTERFACE IN FREE-RADICAL REACTIONS
LOUW, R
PORTER, NA
FREE RADICALS IN SYNTHESIS AND BIOLOGY, 1989, 260 : 469 - 474
[24] FREE-RADICAL CHEMISTRY OF NATURAL-PRODUCTS
NETA, P
SIMIC, MG
FOOD TECHNOLOGY, 1984, 38 (03) : 48 - 49
[25] CHEMISTRY OF FREE-RADICAL AND SINGLET OXIDATION OF LIPIDS
FRANKEL, EN
PROGRESS IN LIPID RESEARCH, 1984, 23 (04) : 197 - 221
[26] WILLIAMS,GH - ADVANCES IN FREE-RADICAL CHEMISTRY
RUCHARDT, C
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (05) : 475 - &
[27] APPLICATIONS OF FREE-RADICAL REACTIONS IN HETEROCYCLIC CHEMISTRY
HEUSLER, K
HETEROCYCLES, 1975, 3 (11) : 1035 - 1064
[28] FREE-RADICAL CHEMISTRY OF SELENIUM CONTAINING COMPOUNDS
BADIELLO, R
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1988, 38 (3-4): : 317 - 325
[29] FREE-RADICAL MECHANISMS IN ORGANOMETALLIC AND BIOORGANOMETALLIC CHEMISTRY
HALPERN, J
PURE AND APPLIED CHEMISTRY, 1986, 58 (04) : 575 - 584
[30] WILLIAMS,GH - ADVANCES IN FREE-RADICAL CHEMISTRY
ROBB, JC
TRANSACTIONS OF THE FARADAY SOCIETY, 1967, 63 (533P): : 1309 - &

← 1 2 3 4 5 →