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

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 11期

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

页码：1649 / 1652

页数：4

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
ANDERSON, MG
JARMAN, TB
RICKARDS, RW
[J]. JOURNAL OF ANTIBIOTICS, 1995, 48 (05) : 391 - 398
[3] MODIFICATION OF THE NICKEL REACTION - A GENERAL SYNTHETIC APPROACH TO 2-VINYL-2,3-DIHYDROBENZOFURANS
BIGI, F
CASIRAGHI, G
CASNATI, G
SARTORI, G
[J]. TETRAHEDRON, 1983, 39 (01) : 169 - 174
[4] Yanuthones:: Novel metabolites from a marine isolate of Aspergillus niger
Bugni, TS
Abbanat, D
Bernan, VS
Maiese, WM
Greenstein, M
Van Wagoner, RM
Ireland, CM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) : 7195 - 7200
[5] 1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES
CHEN, KM
HARDTMANN, GE
PRASAD, K
REPIC, O
SHAPIRO, MJ
[J]. TETRAHEDRON LETTERS, 1987, 28 (02) : 155 - 158
[6] STEREOSPECIFIC SYNTHESIS OF DL-ISOEPOXYDON, A NEW METABOLITE OF IMPORTANCE TO THE PATULIN PATHWAY
CHOU, DTW
GANEM, B
[J]. 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
DAUBEN, WG
COGEN, JM
BEHAR, V
[J]. TETRAHEDRON LETTERS, 1990, 31 (23) : 3241 - 3244
[8] Inhibition of NF-kappa B activation by panepoxydone
Erkel, G
Anke, T
Sterner, O
[J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1996, 226 (01) : 214 - 221
[9] SYNTHESIS OF BROMOXONE
GAUTIER, ECL
LEWIS, NJ
MCKILLOP, A
TAYLOR, RJK
[J]. 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
Gehrt, A
Erkel, G
Anke, T
Sterner, O
[J]. JOURNAL OF ANTIBIOTICS, 1998, 51 (05) : 455 - 463

← 1 2 3 →