Intermolecular C-H activation at benzylic positions:: synthesis of (+)-imperanene and (-)-α-conidendrin

被引：66

作者：

Davies, HML ^{[1
]}

Jin, QH ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 07期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/S0957-4166(03)00154-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An efficient C-H activation of primary benzylic positions by means of rhodium carbenoid induced C-H insertions is described. This key step was used in concise syntheses of (+)-imperanene and (-)-alpha-conidendrin. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：941 / 949

页数：9

共 50 条

[1] RHODIUM ACETATE CATALYZES THE ADDITION OF CARBENOIDS ALPHA-OXYGENS TO ETHER OXYGENS
ADAMS, J
POUPART, MA
GRENIER, L
SCHALLER, C
OUIMET, N
FRENETTE, R
[J]. TETRAHEDRON LETTERS, 1989, 30 (14) : 1749 - 1752
[2] AMBRAMOVITCH RA, 1965, J CHEM SOC CHEM COMM, P542
[3] UNUSUALLY MILD AND SELECTIVE HYDROCARBON C-H BOND ACTIVATION WITH POSITIVELY CHARGED IRIDIUM(III) COMPLEXES
ARNDTSEN, BA
BERGMAN, RG
[J]. SCIENCE, 1995, 270 (5244) : 1970 - 1973
[4] 1ST TOTAL SYNTHESIS OF (-)-ALPHA-CONIDENDRIN
BOISSIN, P
DHAL, R
BROWN, E
[J]. TETRAHEDRON LETTERS, 1989, 30 (33) : 4371 - 4374
[5] HOMOLOGATION OF N-ALKANES USING DIAZOESTERS AND RHODIUM(III)PORPHYRINS - ENHANCED ATTACK ON PRIMARY C-H BONDS
CALLOT, HJ
METZ, F
[J]. TETRAHEDRON LETTERS, 1982, 23 (42) : 4321 - 4324
[6] CALLOT HJ, 1985, NOUV J CHIM, V9, P167
[7] Deracemization of alpha-substituted arylacetic acids
Camps, P
Gimenez, S
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (04) : 1227 - 1234
[8] Thermal, catalytic, regiospecific functionalization of alkanes
Chen, HY
Schlecht, S
Semple, TC
Hartwig, JF
[J]. SCIENCE, 2000, 287 (5460) : 1995 - 1997
[9] C-C bond formation via C-H bond activation: Synthesis of the core of teleocidin B4
Dangel, BD
Godula, K
Youn, SW
Sezen, B
Sames, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) : 11856 - 11857
[10] Cytotoxic responses to aromatic ring and configurational variations in α-conidendrin, podophyllotoxin, and sikkimotoxin derivatives
Dantzig, A
LaLonde, RT
Ramdayal, F
Shepard, RL
Yanai, K
Zhang, MJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (02) : 180 - 185

← 1 2 3 4 5 →