Aryllead(IV) reagents in synthesis:: Formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate

被引：74

作者：

Deng, HB ^{[1
]}

Konopelski, JP ^{[1
]}

机构：

[1] Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 19期

关键词：

D O I：

10.1021/ol016379r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The reaction of lead(IV) 4-indolyl triacetate with substituted methyl 2-oxo-1-cyclohexanecarboxylates has been investigated as a route to the natural product N-methylwelsitindolinone C isothiocyanate. Reaction of lead(IV) reagent 18 with beta -ketoester 20 affords the desired coupled material in excellent yield and diastereoselectivity.

引用

页码：3001 / 3004

页数：4

共 31 条

[1] DIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES
ADAM, W
HADJIARAPOGLOU, L
SMERZ, A
[J]. CHEMISCHE BERICHTE, 1991, 124 (01) : 227 - 232
[2] NONSTEROIDAL ANTIINFLAMMATORY AGENTS .2. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 2-CHLOROINDOLECARBOXYLIC ACIDS
ANDREANI, A
BONAZZI, D
RAMBALDI, M
GUARNIERI, A
ANDREANI, F
STROCCHI, P
MONTANARO, N
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (10) : 1344 - 1346
[3] FUSED INDOLES .1. SYNTHESIS OF 1,9-DIHYDROTHIAZINO[3,4-B]INDOLE RING-SYSTEM
COPPOLA, GM
HARDTMANN, GE
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (06) : 1117 - 1118
[4] DENG H, 2000, 220 NAT M AM CHEM SO
[5] SYNTHESIS OF A NOR-NEOLIGNAN FROM KRAMERIA-RAMOSISSIMA
DONNELLY, DMX
FINET, JP
KIELTY, JM
[J]. TETRAHEDRON LETTERS, 1991, 32 (31) : 3835 - 3836
[6] Arylation with organolead and organobismuth reagents
Elliott, GI
Konopelski, JP
[J]. TETRAHEDRON, 2001, 57 (27) : 5683 - 5705
[7] Diastereoselectivity in the formation of quaternary centers with aryllead(IV) tricarboxylates
Elliott, GI
Konopelski, JP
Olmstead, MM
[J]. ORGANIC LETTERS, 1999, 1 (11) : 1867 - 1870
[8] Finet J. P., 1998, Ligand Coupling Reactions with Heteroatomic Compounds
[9] A CONVENIENT METHOD FOR THE PREPARATION OF 1-(TERT-BUTYLOXYCARBONYL)PYRROLES
GREHN, L
RAGNARSSON, U
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (04): : 296 - &
[10] REACTIONS OF N-BROMOSUCCINIMIDE + INDOLES . SIMPLE SYNTHESIS OF 3-BROMOOXINDOLES
HINMAN, RL
BAUMAN, CP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (05) : 1206 - +

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