Efficient access to orthoquinols and their [4+2] cyclodimers via SIBX-mediated hydroxylative phenol dearomatization

被引：70

作者：

Lebrasseur, Nathalie

Gagnepain, Julien

Ozanne-Beaudenon, Aurelie

Leger, Jean-Michel

Quideau, Stephane

机构：

[1] Univ Bordeaux, Inst Europeen Chim & Biol, F-33607 Pessac, France

[2] Inst Mol Sci, CNRS, UMR 5255, F-33405 Talence, France

[3] Lab Pharmacochim, F-33076 Bordeaux, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 16期

关键词：

D O I：

10.1021/jo0708893

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

SIBX, the nonexplosive formulation of the lambda(5)-iodane 2-iodoxybenzioc acid (IBX), safely and efficiently mediates the hydroxylative dearomatization of various 2-alkylphenols and napthols into orthoquinols or their [4 + 2] cyclodimers. Reactions are typically run at room temperature using SIBX as a suspension in THF. Using these conditions, natural products such as the cyclodimer of the terpene carvacrol and, for the first time, the shikimate-derived (+/-)-grandifloracin were prepared in one step from their respective phenolic precursor.

引用

页码：6280 / 6283

页数：4

共 36 条

[1] Novel DPPH radical scavengers, bisorbicillinol and demethyltrichodimerol, from a fungus [J].

Abe, N ;

Murata, T ;

Hirota, A .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1998, 62 (04) :661-666

[2] PERJODATOXYDATION VON PHENOLEN .7. 2,6-DIMETHYLPHENOL SOWIE 2,4,6-TRIMETHYLPHENOL UND 2,3,5-TRIMETHYLPHENOL [J].

ADLER, E ;

DAHLEN, J ;

WESTIN, G .

ACTA CHEMICA SCANDINAVICA, 1960, 14 (07) :1580-1596

[3] PERIODATE OXIDATION OF PHENOLS .11. DIELS-ALDER REACTIONS OF 2,4-CYCLOHEXADIENONES .1. STRUCTURAL AND STERIC ORIENTATION IN DIMERIZATION OF 2,4-CYCLOHEXADIENONES [J].

ADLER, E ;

HOLMBERG, K .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1974, B 28 (04) :465-472

[4] PERIODATE OXIDATION OF PHENOLS .20. REACTIONS OF 5-SUBSTITUTED 2,4-CYCLOHEXADIENONES WITH DIENOPHILES [J].

ANDERSSON, G .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (05) :403-406

[5] PERIODATE OXIDATION OF PHENOLS .19. NONDIMERIZING ORTHO-QUINOLS, ORTHO-QUINOL ETHERS, AND ORTHO-QUINONE KETALS [J].

ANDERSSON, G .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (01) :64-70

[6] 3,10-DIHYDROXYDIELMENTHA-5,11-DIENE-4,9-DIONE - A DITERPENOID (BISMONOTERPENOID) WITH A NOVEL CARBON SKELETON [J].

CARMAN, RM ;

LAMBERT, LK ;

ROBINSON, WT ;

VANDONGEN, JMAM .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (11) :1843-1850

[7]

DEPERNET D, 2002, Patent No. 20020107416

[8] DEHYDRATION OF DIMERIC 6-HYDROXYCYCLOHEXA-2,4-DIENONES AN ALTERNATIVE COURSE FOR THESE REACTIONS AND A MODEL FOR THE MAYTENONE TO ANHYDROMAYTENONE TRANSFORMATION [J].

FALSHAW, CP ;

FRANKLINOS, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (01) :95-100

[9] Total synthesis of (+)-aquaticol by biomimetic phenol dearomatization:: Double diastereofacial differentiation in the Diels-Alder dimerization of orthoquinols with a C2-symmetric transition state [J].

Gagnepain, Julien ;

Castet, Frederic ;

Quideau, Stephane .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1533-1535

[10] o-iodoxybenzoic acid (IBX):: pKa and proton-affinity analysis [J].

Gallen, Michael J. ;

Goummont, Regis ;

Clark, Timothy ;

Terrier, Francois ;

Williams, Craig M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (18) :2929-2934

← 1 2 3 4 →