Synthesis of 12-deoxyroyleanone, cryptoquinone, 11,14-dihydroxy-8,11,13-abietatrien-7-one, and related derivatives from dehydroabietic acid

被引:21
作者
Matsushita, Y [1 ]
Iwakiri, Y [1 ]
Yoshida, S [1 ]
Sugamoto, K [1 ]
Matsui, T [1 ]
机构
[1] Miyazaki Univ, Fac Engn, Miyazaki 8892192, Japan
关键词
synthesis; dehydroabietic acid; 12-deoxyroyleanone; cryptoquinone; 11,14-dihydroxyabieta-8,11,13-trien-7-one;
D O I
10.1016/j.tetlet.2005.03.170
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Naturally occurring abietane quinones and hydroquinone, namely, 12-deoxyroyleanone (1a), cryptoquinone (4a), and 11,14-dihydroxyabieta-8,11,13-trien-7-one (5a), together with the epimers of tryptoquinones D (2) and F (3), were first synthesized from dehydroalbietic acid (6). © 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3629 / 3632
页数:4
相关论文
共 39 条
[1]  
AKITA H, 1981, CHEM PHARM BULL, V29, P1567
[2]   SIMPLE AND CONVENIENT DEAMINATION OF AROMATIC-AMINES [J].
CADOGAN, JIG ;
MOLINA, GA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (06) :541-542
[3]   A synthesis of triptoquinones D, E, and F from podocarpic acid [J].
Cambie, RC ;
Mitchell, LH ;
Rutledge, PS .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1998, 51 (10) :931-940
[4]   Substitution reactions of dehydroabietic acid. II [J].
Campbell, WP ;
Morgana, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 :1838-1843
[5]   Rates and mechanisms of the thermal solvolytic decomposition of arenediazonium ions [J].
Canning, PSJ ;
McCrudden, K ;
Maskill, H ;
Sexton, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (12) :2735-2740
[6]   REDUCTIVE DEAMINATION OF ARYLAMINES BY ALKYL NITRITES IN N,N-DIMETHYLFORMAMIDE - DIRECT CONVERSION OF ARYLAMINES TO AROMATIC-HYDROCARBONS [J].
DOYLE, MP ;
DELLARIA, JF ;
SIEGFRIED, B ;
BISHOP, SW .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (22) :3494-3498
[7]   New resin acid derivatives: Diisocyanate, diurethanes and diureides [J].
Gigante, B ;
Esteves, MA ;
Curto, MJM ;
Ascenso, J ;
Prabhakar, S ;
Lobo, AM .
SYNTHETIC COMMUNICATIONS, 1998, 28 (04) :639-652
[8]   AN IMPROVED PROCEDURE FOR THE DEAMINATION OF 5-AMINOTETRAZOLE [J].
HENRY, RA ;
FINNEGAN, WG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (01) :290-291
[9]   A NEW SYNTHESIS OF METHOXYINDOLES [J].
HUNT, RR ;
RICHARD, RL .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (03) :344-&
[10]   RUTHENIUM-CATALYZED OXIDATION OF PHENOLS WITH HYDROGEN-PEROXIDE [J].
ITO, S ;
AIHARA, K ;
MATSUMOTO, M .
TETRAHEDRON LETTERS, 1983, 24 (47) :5249-5252