Exploring chemical diversity of epoxyquinoid natural products: Synthesis and biological activity of (-)-jesterone and related molecules

被引:78
作者
Hu, YB
Li, CM
Kulkarni, BA
Strobel, G
Lobkovsky, E
Torczynski, RM
Porco, JA
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Ctr Streamlined Synth, Metcalf Ctr Sci & Engn, Boston, MA 02215 USA
[3] Montana State Univ, Dept Plant Sci, Bozeman, MT 59717 USA
[4] Cornell Univ, Baker Lab, Dept Chem, Ithaca, NY 14853 USA
[5] Cytoclonal Pharmaceut Inc, Dallas, TX 75235 USA
关键词
D O I
10.1021/ol0159367
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Enantioselective syntheses of the potent antifungal agent (-)-jesterone, its hydroxy epimer, and a dimeric quinone epoxide derivative are reported. The synthesis involves diastereoselective epoxidation of a chiral quinone monoketal derivative and regio and stereoselective reduction of a quinone epoxide intermediate.
引用
收藏
页码:1649 / 1652
页数:4
相关论文
共 28 条
[1]  
ALCARAZ L, 1998, SYNTHESIS-STUTTGART, V15, P775
[2]   STRUCTURES AND ABSOLUTE-CONFIGURATIONS OF ANTIBIOTICS OF THE OLIGOSPORON GROUP FROM THE NEMATODE-TRAPPING FUNGUS ARTHROBOTRYS OLIGOSPORA [J].
ANDERSON, MG ;
JARMAN, TB ;
RICKARDS, RW .
JOURNAL OF ANTIBIOTICS, 1995, 48 (05) :391-398
[3]   MODIFICATION OF THE NICKEL REACTION - A GENERAL SYNTHETIC APPROACH TO 2-VINYL-2,3-DIHYDROBENZOFURANS [J].
BIGI, F ;
CASIRAGHI, G ;
CASNATI, G ;
SARTORI, G .
TETRAHEDRON, 1983, 39 (01) :169-174
[4]   Yanuthones:: Novel metabolites from a marine isolate of Aspergillus niger [J].
Bugni, TS ;
Abbanat, D ;
Bernan, VS ;
Maiese, WM ;
Greenstein, M ;
Van Wagoner, RM ;
Ireland, CM .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) :7195-7200
[5]   1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].
CHEN, KM ;
HARDTMANN, GE ;
PRASAD, K ;
REPIC, O ;
SHAPIRO, MJ .
TETRAHEDRON LETTERS, 1987, 28 (02) :155-158
[6]   STEREOSPECIFIC SYNTHESIS OF DL-ISOEPOXYDON, A NEW METABOLITE OF IMPORTANCE TO THE PATULIN PATHWAY [J].
CHOU, DTW ;
GANEM, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (27) :7987-7988
[7]   CLAY CATALYZED REARRANGEMENT OF SUBSTITUTED ALLYL PHENYL ETHERS - SYNTHESIS OF ORTHO-ALLYL PHENOLS, CHROMANS AND COUMARANS [J].
DAUBEN, WG ;
COGEN, JM ;
BEHAR, V .
TETRAHEDRON LETTERS, 1990, 31 (23) :3241-3244
[8]   Inhibition of NF-kappa B activation by panepoxydone [J].
Erkel, G ;
Anke, T ;
Sterner, O .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1996, 226 (01) :214-221
[9]   SYNTHESIS OF BROMOXONE [J].
GAUTIER, ECL ;
LEWIS, NJ ;
MCKILLOP, A ;
TAYLOR, RJK .
TETRAHEDRON LETTERS, 1994, 35 (47) :8759-8760
[10]   Cycloepoxydon, 1-hydroxy-2-hydroxymethyl-3-pent-1-enylbenzene and 1-hydroxy-2-hydroxymethyl-3-pent-1,3-dienylbenzene, new inhibitors of eukaryotic signal transduction [J].
Gehrt, A ;
Erkel, G ;
Anke, T ;
Sterner, O .
JOURNAL OF ANTIBIOTICS, 1998, 51 (05) :455-463