Total synthesis of pawhuskin C:: a directed ortho metalation approach

被引：24

作者：

Neighbors, JD ^{[1
]}

Salnikova, MS ^{[1
]}

Wiemer, DF ^{[1
]}

机构：

[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 08期

关键词：

pawhuskin; directed ortho metalation;

D O I：

10.1016/j.tetlet.2004.12.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the opioid modulator pawhuskin C has been accomplished in eight steps from methyl 3,5-dihydroxybenzoate. The key step in this sequence is a directed ortho metalation reaction conducted without protection of a benzylic alcohol and thus presumed to involve a formal dianion intermediate. (C) 2005 Elsevier Ltd. All rights reserved.

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页码：1321 / 1324

页数：4

相关论文

共 12 条

[1] New geranyl stilbenes from Dalea purpurea with in vitro opioid receptor affinity [J].

Belofsky, G ;

French, AN ;

Wallace, DR ;

Dodson, SL .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (01) :26-30

[2] Cytotoxic geranyl stilbenes from Macaranga schweinfurthii [J].

Beutler, JA ;

Shoemaker, RH ;

Johnson, T ;

Boyd, MR .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (12) :1509-1512

[3] Schweinfurthin D, a cytotoxic stilbene from Macaranga schweinfurthii [J].

Beutler, JA ;

Jato, J ;

Cragg, GM ;

Boyd, MR .

NATURAL PRODUCT LETTERS, 2000, 14 (05) :399-404

[4] Synthesis and complement inhibitory activity of B/C/D-ring analogues of the fungal metabolite 6,7-diformyl-3′,4′,4a′,5′,6′,7′,8′,8a′-octahydro-4,6′,7′-trihydroxy-2′,5′,5′,8a′-tetramethylspiro[1′(2′H)-naphthalene-2(3H)-benzofuran] [J].

Bradbury, BJ ;

Bartyzel, P ;

Kaufman, TS ;

Nieto, MJ ;

Sindelar, RD ;

Scesney, SM ;

Gaumond, BR ;

Marsh, HC .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (13) :2697-2705

[5]

NEIGHBORS JD, 2005, IN PRESS J ORG CHEM

[6] Selective para metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with n-butyl lithium-potassium tert-butoxide (LIC-KOR):: synthesis of 3,5-dimethoxy-4-methyl benzoic acid [J].

Sinha, S ;

Mandal, B ;

Chandrasekaran, S .

TETRAHEDRON LETTERS, 2000, 41 (17) :3157-3160

[7] Synthesis of Schweinfurthin C, a geranylated stilbene from Macaranga schweinfurthii [J].

Treadwell, EM ;

Cermak, SC ;

Wiemer, DF .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23) :8718-8723

[8] THE ATOM ECONOMY - A SEARCH FOR SYNTHETIC EFFICIENCY [J].

TROST, BM .

SCIENCE, 1991, 254 (5037) :1471-1477

[9] REGIOCONTROLLED SYNTHESIS OF HYDROXYPHTHALIDES - SYNTHESIS OF (+/-)-ISOOCHRACINIC ACID AND A ZEALERANONE INTERMEDIATE [J].

TROST, BM ;

RIVERS, GT ;

GOLD, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10) :1835-1838

[10] SELECTIVE NUCLEAR LITHIATION OF AROMATIC-COMPOUNDS - FACILE SYNTHESIS OF METHOXYPHTHALIDE DERIVATIVES BY CARBOXYLATION OF LITHIO-COMPOUNDS [J].

UEMURA, M ;

TOKUYAMA, S ;

SAKAN, T .

CHEMISTRY LETTERS, 1975, (11) :1195-1198