Efficient stereoselective syntheses of isopanepoxydone and panepoxydone: a re-assignment of relative configuration

被引：28

作者：

Shotwell, JB

Hu, SJ

Medina, E

Abe, M

Cole, R

Crews, CM ^{[1
]}

Wood, JL

机构：

[1] Yale Univ, Dept Mol Cellular & Dev Biol, New Haven, CT 06520 USA

[2] Yale Univ, Sterling Chem Lab, New Haven, CT 06520 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(00)01736-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Recent efforts in our laboratories have resulted in efficient racemic syntheses of isopanepoxydone and panepoxydone, secondary metabolites isolated originally from the basidiomycete Panus conchatus. These synthetic efforts have led us to assign the structure of isopanepoxydone as that of 3 and re-assign the structure of panepoxydone as 2. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：9639 / 9643

页数：5

相关论文

共 14 条

[1] 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

[2] New stereoselective route to the epoxyquinol core of manumycin-type natural products. synthesis of enantiopure (+)-bromoxone, (-)-LL-C10037α, and (+)-KT 8110 [J].

Block, O ;

Klein, G ;

Altenbach, HJ ;

Brauer, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :716-721

[3] SILYL MIGRATION AND FORMATION OF AN ANHYDRO DERIVATIVE ON ATTEMPTED BENZYLATION OF 3-O-TERT-BUTYLDIMETHYLSILYL-6-O-TOSYL-D-GLUCAL [J].

CRICH, D ;

RITCHIE, TJ .

CARBOHYDRATE RESEARCH, 1990, 197 :324-326

[4] 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

[5] SYNTHESIS OF BROMOXONE [J].

GAUTIER, ECL ;

LEWIS, NJ ;

MCKILLOP, A ;

TAYLOR, RJK .

TETRAHEDRON LETTERS, 1994, 35 (47) :8759-8760

[6] 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

[7] RETRO [1,4]-BROOK REARRANGEMENTS OF NONCONJUGATED SECONDARY ALPHA-LITHIO ETHERS - PROOF OF STEREOSPECIFICITY AND OF RETENTION OF CONFIGURATION AT THE CARBANION CENTER [J].

HOFFMANN, R ;

BRUCKNER, R .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (12) :2731-2739

[8] ISOLATION AND STRUCTURE ELUCIDATION OF ANTIPHENICOL, AN ANTAGONIST OF CHLORAMPHENICOL [J].

IMAGAWA, Y ;

SHIMA, S ;

HIROTA, A ;

SAKAI, H .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1979, 43 (12) :2437-2440

[9] ENZYMATIC RESOLUTION OF A C-2 SYMMETRICAL DIOL DERIVED FROM P-BENZOQUINONE - SYNTHESIS OF (+)-BROMOXONE AND (-)-BROMOXONE [J].

JOHNSON, CR ;

MILLER, MW .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6674-6675

[10]

KELLER R, 1979, CHEM BER-RECL, V112, P3347, DOI 10.1002/cber.19791121006