Total synthesis of the novel angiogenesis inhibitors epoxyquinols A and B

被引:58
作者
Mehta, G [1 ]
Islam, K [1 ]
机构
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
D O I
10.1016/S0040-4039(03)00621-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the recently discovered angiogenesis inhibitors epoxyquinols A and B, having novel polyketide derived dimeric structures, has been accomplished from the readily available Diels-Alder adduct of cyclopentadiene and p-benzoquinone through a short, simple and flexible strategy that is diversity oriented and can be adapted to an asymmetric variant. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3569 / 3572
页数:4
相关论文
共 16 条
[1]   PHOTOCHEMICAL CYCLISATION OF DIELS-ALDER ADDUCTS [J].
COOKSON, RC ;
CRUNDWELL, E ;
HILL, RR ;
HUDEC, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (SEP) :3062-&
[2]   The rationale and future potential of angiogenesis inhibitors in neoplasia [J].
Gasparini, G .
DRUGS, 1999, 58 (01) :17-38
[3]   The synthesis of epi-epoxydon utilising the Baylis-Hillman reaction [J].
Genski, T ;
Taylor, RJK .
TETRAHEDRON LETTERS, 2002, 43 (19) :3573-3576
[4]   Epoxyquinol A, a highly functionalized pentaketide dimer with antiangiogenic activity isolated from fungal metabolites [J].
Kakeya, H ;
Onose, R ;
Koshino, H ;
Yoshida, A ;
Kobayashi, K ;
Kageyama, S ;
Osada, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3496-3497
[5]   Epoxyquinol B, a fungal metabolite with a potent antiangiogenic activity [J].
Kakeya, H ;
Onose, R ;
Yoshida, A ;
Koshino, H ;
Osada, H .
JOURNAL OF ANTIBIOTICS, 2002, 55 (09) :829-831
[6]   The enantiocontrolled synthesis of (-)-tricholomenyn A, a novel antimitotic enynylcyclohexenone from Tricholoma acerbum [J].
Kamikubo, T ;
Ogasawara, K .
CHEMICAL COMMUNICATIONS, 1996, (14) :1679-1680
[7]   Stereo- and enantio-controlled synthesis of two naturally occurring polyoxygenated cyclohexenemethanols, (+)-epiepoxydon and (-)-phyllostine, via catalytic asymmetrization of a meso substrate [J].
Kamikubo, T ;
Hiroya, K ;
Ogasawara, K .
TETRAHEDRON LETTERS, 1996, 37 (04) :499-502
[8]   1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES WITH DIISOBUTYLALUMINUM HYDRIDE AND TRIBUTYLTIN HYDRIDE [J].
KIYOOKA, S ;
KURODA, H ;
SHIMASAKI, Y .
TETRAHEDRON LETTERS, 1986, 27 (26) :3009-3012
[9]   Angiogenesis inhibitor epoxyquinol A:: Total synthesis and inhibition of transcription factor NF-κB [J].
Li, CM ;
Bardhan, S ;
Pace, EA ;
Liang, MC ;
Gilmore, TD ;
Porco, JA .
ORGANIC LETTERS, 2002, 4 (19) :3267-3270
[10]   Total synthesis of (±)-torreyanic acid [J].
Li, CM ;
Lobkovsky, E ;
Porco, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (42) :10484-10485