Tin-assisted cyclization for chiral cyclohexane synthesis, an alternative route to (-)-tetrodotoxin skeleton

被引：21

作者：

Bamba, M ^{[1
]}

Nishikawa, T ^{[1
]}

Isobe, M ^{[1
]}

机构：

[1] NAGOYA UNIV,SCH AGR SCI,ORGAN CHEM LAB,NAGOYA,AICHI 46401,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 45期

关键词：

D O I：

10.1016/0040-4039(96)01860-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A carbon framework including chiral cyclohexane was synthesized as a possible intermediate for tetrodotoxin. The key steps were electrocyclization of the precursor triene derivatives. Smooth cyclization resulted especially with tributyltin derivative due to an attractive interaction with the 2-oxygen function. The corresponding triethylsilyl derivative scarcely reacted due to rather repulsive interaction. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：8199 / 8202

页数：4

共 19 条

[1] CARBOHYDRATES TO CARBOCYCLES - SYNTHESIS OF THE DENSELY FUNCTIONALIZED CARBOCYCLIC CORE OF TETRODOTOXIN BY RADICAL CYCLIZATION OF AN ANHYDRO SUGAR PRECURSOR [J].

ALONSO, RA ;

BURGEY, CS ;

RAO, BV ;

VITE, GD ;

VOLLERTHUN, R ;

ZOTTOLA, MA ;

FRASERREID, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6666-6672

[2] CONCERNING THE FORMATIONS OF ALPHA-IODOENONES [J].

BOVONSOMBAT, P ;

ANGARA, GJ ;

MCNELIS, E .

TETRAHEDRON LETTERS, 1994, 35 (37) :6787-6790

[3] Armed disarmed effects and adamantyl expansion of some caged tricyclic acetals en route to tetrodotoxin [J].

Burgey, CS ;

Vollerthun, R ;

FraserReid, B .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1609-1618

[4]

FRASERREID B, 1992, B SOC CHIM BELG, V101, P617

[5]

HOSOMI A, 1979, TETRAHEDRON LETT, V20, P429

[6] DIRECT ALPHA-IODINATION OF CYCLOALKENONES [J].

JOHNSON, CR ;

ADAMS, JP ;

BRAUN, MP ;

SENANAYAKE, CBW ;

WOVKULICH, PM ;

USKOKOVIC, MR .

TETRAHEDRON LETTERS, 1992, 33 (07) :917-918

[7] REGIOSELECTIVE HYDROSTANNATION OF TERMINAL ACETYLENES UNDER TRANSITION-METAL CATALYSIS [J].

KIKUKAWA, K ;

UMEKAWA, H ;

WADA, F ;

MATSUDA, T .

CHEMISTRY LETTERS, 1988, (05) :881-884

[8] SYNTHETIC STUDIES ON TETRODOTOXIN AND RELATED COMPOUNDS .3. STEREOSPECIFIC SYNTHESIS OF AN EQUIVALENT OF ACETYLATED TETRODAMINE [J].

KISHI, Y ;

ARATANI, M ;

FUKUYAMA, T ;

NAKATSUB.F ;

GOTO, T ;

INOUE, S ;

TANINO, H ;

SUGIURA, S ;

KAKOI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (26) :9217-9219

[9] SYNTHETIC STUDIES ON TETRODOTOXIN AND RELATED COMPOUNDS .4. STEREOSPECIFIC TOTAL SYNTHESES OF DL-TETRODOTOXIN [J].

KISHI, Y ;

FUKUYAMA, T ;

ARATANI, M ;

NAKATSUB.F ;

GOTO, T ;

INOUE, S ;

TANINO, H ;

SUGIURA, S ;

KAKOI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (26) :9219-9221

[10] STUDIES IN GROUP 4 ORGANOMETALLIC CHEMISTRY .24. STRUCTURE OF PRODUCTS OBTAINED IN HYDROSTANNATION OF ETHYNES [J].

LEUSINK, AJ ;

BUDDING, HA ;

MARSMAN, JW .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 9 (02) :285-&

← 1 2 →