First synthesis of (±)-1α,2α,4β-trihydroxycyclohex-5-ene.: Anchimeric assistance in conduritol syntheses.

被引：22

作者：

Haines, AH ^{[1
]}

King, ASH ^{[1
]}

Knight, JR ^{[1
]}

Nguyen, VA ^{[1
]}

机构：

[1] Univ E Anglia, Sch Chem Sci, Norwich NR4 7TJ, Norfolk, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(98)00745-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The deoxy-conduritol (1 alpha,2 alpha,4 beta)-1,2,4-trihydroxycyclohex-5-ene (6) has been prepared in racemic form from 1,4-benzoquinone in a six-step sequence, the key reaction involving a monohalide displacement by anchimeric assistance in the diacetoxy-dibromo compound previously employed for a synthesis of conduritol-B. Evidence for the mechanism of the double halide displacement in the latter synthesis has been obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4393 / 4396

页数：4

共 17 条

[1] CONDURITOLS AND RELATED-COMPOUNDS
BALCI, M
SUTBEYAZ, Y
SECEN, H
[J]. TETRAHEDRON, 1990, 46 (11) : 3715 - 3742
[2] SYNTHESIS OF (5,6)-EPOXY-(1-ALPHA, 2-BETA, 3-ALPHA, 4-BETA)-(+)-5-CYCLOHEXANE- 1-H-3, 2,3, 4-H-3 -TETROL - (H-3 CONDURITOL-B EPOXIDE)
GAL, AE
VOORSTAD, JP
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1987, 24 (04) : 397 - 407
[3] GUNSTONE FD, 1960, ADVANCES ORGANIC CHE, V1, P103
[4] IMPROVED PREPARATION OF (+/-)-(1,3/2,4)-5-CYCLOHEXENE-1,2,3,4-TETROL [(+/-)-CONDURITOL-B] AND ITS REACTION WITH HYDROBROMIC AND HYDROCHLORIC-ACID - SYNTHESIS AND CHARACTERIZATION OF SOME (+/-)-1,4-DIDEOXY-1-HALO-CONDURITOL AND (+/-)-1,4-DIDEOXY-1,4-DIHALO-CONDURITOL
GUO, ZX
HAINES, AH
PYKE, SM
PYKE, SG
TAYLOR, RJK
[J]. CARBOHYDRATE RESEARCH, 1994, 264 (01) : 147 - 153
[5] KNIGHT JR, 1996, SYNTHETIC STUDIES CO
[6] ENANTIOMERICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGARS) AS SYNTHETIC INTERMEDIATES .11. TOTAL SYNTHESES OF (-)-CONDURITOL-B ((-)-1L-CYCLOHEX-5-ENE-1,3/2,4-TETROL) AND OF (+)-CONDURITOL-F ((+)-1D-CYCLOHEX-5-ENE-1,2,4/3-TETROL) - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF (+)-LEUCANTHEMITOL
LEDRIAN, C
VIONNET, JP
VOGEL, P
[J]. HELVETICA CHIMICA ACTA, 1990, 73 (01) : 161 - 168
[7] CATALYTIC PHOTOINDUCED CHARGE-TRANSFER OSMYLATION - A NOVEL PATHWAY FROM ARENES TO CYCLITOL DERIVATIVES
MOTHERWELL, WB
WILLIAMS, AS
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (18): : 2031 - 2033
[8] Chiral base-mediated rearrangement of meso-cyclohexene oxides to allylic alcohols
OBrien, P
Poumellec, P
[J]. TETRAHEDRON LETTERS, 1996, 37 (44) : 8057 - 8058
[9] Prévost C, 1933, CR HEBD ACAD SCI, V196, P1129
[10] PREVOST C, 1933, CR HEBD ACAD SCI, V197, P1661

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