STEREOSELECTIVE SYNTHESIS OF A KLM RING MODEL OF CIGUATOXIN - CONFIRMATION OF THE C54 STEREOCHEMISTRY

被引：35

作者：

SASAKI, M ^{[1
]}

HASEGAWA, A ^{[1
]}

TACHIBANA, K ^{[1
]}

机构：

[1] UNIV TOKYO,SCH SCI,DEPT CHEM,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(00)61366-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A ciguatoxin KLM ring model and its C54 epimer were stereoselectively synthesized. Comparison of their H-1 NMR data with that on the natural toxin established the earlier stereochemical assignment at the C54 position.

引用

页码：8489 / 8492

页数：4

共 20 条

[1] A UNIFIED STEREOCHEMICAL MODEL FOR THE POLYEPOXIDE CYCLIZATION ROUTE TO MARINE POLYETHER TOXINS [J].

ALVAREZ, E ;

RODRIGUEZ, ML ;

ZURITA, D ;

MARTIN, JD .

TETRAHEDRON LETTERS, 1991, 32 (20) :2253-2254

[2] MODEL STUDIES DIRECTED TOWARDS MICROALGAL POLYETHER TOXINS - USE OF 2-PHENYL-SULFONYL CYCLIC ETHERS IN THE PREPARATION OF TRANS, SYN, TRANS ALPHA-ALKYL, BETA-HYDROXY-SUBSTITUTED TETRAHYDROPYRAN SUBUNITS [J].

ALVAREZ, E ;

RICO, M ;

RODRIGUEZ, RM ;

ZURITA, D ;

MARTIN, JD .

TETRAHEDRON LETTERS, 1992, 33 (23) :3385-3388

[3] MODEL STUDIES DIRECTED TOWARDS MICROALGA POLYETHER TOXINS - A STEREOSELECTIVE ENTRY INTO C8 OXEPANE SUBUNITS [J].

ALVAREZ, E ;

DIAZ, MT ;

PEREZ, R ;

MARTIN, JD .

TETRAHEDRON LETTERS, 1991, 32 (20) :2241-2244

[4] MODEL STUDIES DIRECTED TOWARDS MICROALGA POLYETHER TOXINS - A STEREOSELECTIVE ENTRY INTO C10 CIS-FUSED AND TRANS-FUSED OXANE-OXEPANE SUBUNITS [J].

ALVAREZ, E ;

ZURITA, D ;

MARTIN, JD .

TETRAHEDRON LETTERS, 1991, 32 (20) :2245-2248

[5]

COREY EJ, 1972, TETRAHEDRON LETT, P3769

[6] ENANTIOSELECTIVE VICINAL HYDROXYLATION OF TERMINAL AND E-1,2-DISUBSTITUTED OLEFINS BY A CHIRAL COMPLEX OF OSMIUM TETRAOXIDE - AN EFFECTIVE CONTROLLER SYSTEM AND A RATIONAL MECHANISTIC MODEL [J].

COREY, EJ ;

JARDINE, PD ;

VIRGIL, S ;

YUEN, PW ;

CONNELL, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9243-9244

[7]

Deslongchamps P., 1983, STEREOELECTRONIC EFF

[8] BINDING OF BREVETOXINS AND CIGUATOXIN TO THE VOLTAGE-SENSITIVE SODIUM-CHANNEL AND CONFORMATIONAL-ANALYSIS OF BREVETOXIN-B [J].

GAWLEY, RE ;

REIN, KS ;

KINOSHITA, M ;

BADEN, DG .

TOXICON, 1992, 30 (07) :780-785

[9] CIGUATOXIN-2 IS A DIASTEREOMER OF CIGUATOXIN-3 [J].

LEWIS, RJ ;

NORTON, RS ;

BRERETON, IM ;

ECCLES, CD .

TOXICON, 1993, 31 (05) :637-643

[10] C-13 NMR ASSIGNMENTS OF CIGUATOXIN BY INVERSE-DETECTED 2D-SPECTROSCOPY AND AN EXPLANATION OF NMR SIGNAL BROADENING [J].

MURATA, M ;

LEGRAND, AM ;

SCHEUER, PJ ;

YASUMOTO, T .

TETRAHEDRON LETTERS, 1992, 33 (04) :525-526

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