Synthesis of (-)-pregaliellalactone, conversion of (-)-pregaliellalactone to (-)-galiellalactone by mycelia of Galiella rufa

被引：28

作者：

Johansson, M

Köpcke, B

Anke, H

Sterner, O

机构：

[1] Lund Univ, Dept Organ & Bioorgan Chem, SE-22100 Lund, Sweden

[2] IBWF, Inst Biotechnol & Drug Res, D-67663 Kaiserslautern, Germany

来源：

TETRAHEDRON | 2002年 / 58卷 / 13期

关键词：

Diels-Alder cyclisation; Galiella rufa; stannylation; pregaliellalactone; galiellalactone;

D O I：

10.1016/S0040-4020(02)00134-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of (-)-pregaliellalactone (1), a biosynthetic precursor of the potent fungal metabolite ( -)-galiellalactone (3) produced by several ascomycetes, is reported. When fed to a culture of Galiella rufa, 1 was efficiently converted to 3. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2523 / 2528

页数：6

相关论文

共 43 条

[1]

ANKE H, 1990, 7 INT C PEST CHEM, V1, P1

[2] SYNTHESIS OF VARIOUSLY 2-SUBSTITUTED ALKYL (Z)-2-ALKENOATE AND (E)-2-ALKENOATE AND (Z)-ALPHA-YLIDENE-GAMMA-BUTYROLACTONE AND (E)-ALPHA-YLIDENE-GAMMA-BUTYROLACTONE VIA PALLADIUM-MEDIATED CROSS-COUPLING REACTIONS BETWEEN ORGANOSTANNANES AND ORGANIC HALIDES [J].

BELLINA, F ;

CARPITA, A ;

DESANTIS, M ;

ROSSI, R .

TETRAHEDRON, 1994, 50 (41) :12029-12046

[3] Radical hydrostannylation, Pd(0)-catalyzed hydrostannylation, stannylcupration of propargyl alcohols and enynols: Regio- and stereoselectivities [J].

Betzer, JF ;

Delaloge, F ;

Muller, B ;

Pancrazi, A ;

Prunet, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7768-7780

[4] SELECTIVE REDUCTIONS .40. A CRITICAL-EXAMINATION OF THE RELATIVE EFFECTIVENESS OF VARIOUS REDUCING AGENTS FOR THE ASYMMETRIC REDUCTION OF DIFFERENT CLASSES OF KETONES [J].

BROWN, HC ;

PARK, WS ;

CHO, BT ;

RAMACHANDRAN, PV .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5406-5412

[5] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[6] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

[7]

COWELL A, 1979, TETRAHEDRON LETT, P133

[8] ADDITION OF ZINC HOMOENOLATES TO ACETYLENIC ESTERS AND AMIDES - A FORMAL [3+2] CYCLOADDITION [J].

CRIMMINS, MT ;

NANTERMET, PG ;

TROTTER, BW ;

VALLIN, IM ;

WATSON, PS ;

MCKERLIE, LA ;

REINHOLD, TL ;

CHEUNG, AWH ;

STETSON, KA ;

DEDOPOULOU, D ;

GRAY, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1038-1047

[9] Synthesis of (+/-)-licarin B and eupomatenoids-1 and -12: A general approach to 2-aryl-7-alkoxy-benzofuranoid neolignans [J].

Engler, TA ;

Chai, WY .

TETRAHEDRON LETTERS, 1996, 37 (39) :6969-6970

[10] PALLADIUM-CATALYZED COUPLING OF ARYLSTANNANES WITH ORGANIC SULFONATES - A COMPREHENSIVE STUDY [J].

FARINA, V ;

KRISHNAN, B ;

MARSHALL, DR ;

ROTH, GP .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5434-5444

← 1 2 3 4 5 →