Easy Access to (±)-Schefflone and Espintanol

被引：8

作者：

Osipov, Dmitry V. ^{[1
]}

Osyanin, Vitaly A. ^{[1
]}

Klimochkin, Yuri N. ^{[1
]}

机构：

[1] Samara State Tech Univ, Dept Organ Chem, Samara 443100, Russia

来源：

SYNLETT | 2012年 / 06期

关键词：

(+/-)-schefflone; ortho-quinone methide; espintanol; trimerization; Diels-Alder reaction; AROMATIC MONOTERPENE ESPINTANOL; QUINONE METHIDES; THERMOLYSIS; GENERATION; PRECURSORS;

D O I：

10.1055/s-0031-1290611

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidation of espintanol by silver oxide gives trimeric monoterpenoid (+/-)-schefflone via ortho-quinone methide intermediate. The heating of 6-[(dibenzylamino)methyl]-3-isopropyl-2,4-dimethoxyphenol also results in ortho-quinone methide intermediate which is trapped by 3-(dimethylamino)-5,5-dimethylcyclohex-2-en-1-one or benzotriazole.

引用

页码：917 / 919

页数：3

共 20 条

[1] X-RAY CRYSTAL AND MOLECULAR-STRUCTURE OF A TRIMERIC ORTHO-QUINONE METHIDE DERIVED FROM 2,6-DIBROMOMETHYL-4-METHYLPHENYL [J].

BAVOUX, C ;

PERRIN, M ;

GOLDMANN, H ;

BOHMER, V .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (12) :2059-2063

[2] GENERATION OF ORTHO-QUINONE METHIDES IN SOLUTION - TRIMERIZATION [J].

BOLON, DA .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (03) :715-&

[3] APPROACH TO THE SYNTHESIS OF CANDELABRONE AND SYNTHESIS OF 3,7-DIKETO-12-HYDROXYABIETA-8,11,13-TRIENE [J].

BURNELL, RH ;

CARON, S .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (05) :1446-1454

[4] SPIRANS .15. THE EFFECT OF RING SIZE UPON THE REGIOSELECTIVE OXIDATIVE COUPLING OF HETEROCYCLIC PHENOLS [J].

DEAN, FM ;

ORABI, MOA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (11) :2617-2624

[5]

FAURE R, 1991, B SOC CHIM FR, P378

[6] ISOLATION AND SYNTHESIS OF ESPINTANOL, NEW ANTIPARASITIC MONOTERPENE [J].

HOCQUEMILLER, R ;

CORTES, D ;

ARANGO, GJ ;

MYINT, SH ;

CAVE, A ;

ANGELO, A ;

MUNOZ, V ;

FOURNET, A .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02) :445-452

[7]

Kokwaro J. O., 2009, MED PLANTS E AFRICA, P43

[8] ENONE MESYLATES - PRECURSORS TO BETA-SUBSTITUTED CYCLOHEXENONES [J].

KOWALSKI, CJ ;

FIELDS, KW .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (01) :197-201

[9] Efficient Generation of ortho-Quinone Methide: Application to the Biomimetic Syntheses of (±)-Schefflone and Tocopherol Trimers [J].

Liao, Daohong ;

Li, Houhua ;

Lei, Xiaoguang .

ORGANIC LETTERS, 2012, 14 (01) :18-21

[10] (±)-schefflone:: a trimeric monoterpenoid from the root bark of Uvaria scheffleri [J].

Nkunya, MHH ;

Jonker, SA ;

de Gelder, R ;

Wachira, SW ;

Kihampa, C .

PHYTOCHEMISTRY, 2004, 65 (04) :399-404

← 1 2 →