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
BAVOUX, C
PERRIN, M
GOLDMANN, H
BOHMER, V
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (12): : 2059 - 2063
[2] GENERATION OF ORTHO-QUINONE METHIDES IN SOLUTION - TRIMERIZATION
BOLON, DA
[J]. 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
BURNELL, RH
CARON, S
[J]. 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
DEAN, FM
ORABI, MOA
[J]. 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
HOCQUEMILLER, R
CORTES, D
ARANGO, GJ
MYINT, SH
CAVE, A
ANGELO, A
MUNOZ, V
FOURNET, A
[J]. 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
KOWALSKI, CJ
FIELDS, KW
[J]. 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
Liao, Daohong
Li, Houhua
Lei, Xiaoguang
[J]. ORGANIC LETTERS, 2012, 14 (01) : 18 - 21
[10] (±)-schefflone:: a trimeric monoterpenoid from the root bark of Uvaria scheffleri
Nkunya, MHH
Jonker, SA
de Gelder, R
Wachira, SW
Kihampa, C
[J]. PHYTOCHEMISTRY, 2004, 65 (04) : 399 - 404

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