Synthesis of the C6-C16 polyene fragment of ratjadone, a potent cytotoxic metabolite from Sorangium cellulosum

被引:14
作者
Claus, E [1 ]
Kalesse, M [1 ]
机构
[1] Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
关键词
D O I
10.1016/S0040-4039(99)00716-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Pd-catalyzed synthesis of the polyene fragment of ratjadone is described. This strategy employs the Stille-coupling for the coupling of the tetrahydropyran subunit and the Suzuki coupling for attaching the unsaturated lactone to the polyene chain. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
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页码:4157 / 4160
页数:4
相关论文
共 19 条
[1]  
Arimoto H, 1998, SYNLETT, P765
[2]   Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes [J].
Boden, CDJ ;
Pattenden, G ;
Ye, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (20) :2417-2419
[3]   A STEREOSPECIFIC SYNTHESIS OF CONJUGATED (E,Z)-ALKADIENES AND (E,E)-ALKADIENES BY THE PALLADIUM-CATALYZED REACTION OF (E)-1-ALKENYLBORONIC ACIDS AND 1-ALKENYL IODIDES [J].
CASSANI, G ;
MASSARDO, P ;
PICCARDI, P .
TETRAHEDRON LETTERS, 1983, 24 (24) :2513-2516
[4]   PREPARATION AND USE OF 1-IODOALKYL YLIDES [J].
CHEN, J ;
WANG, T ;
ZHAO, K .
TETRAHEDRON LETTERS, 1994, 35 (18) :2827-2828
[5]   RATJADON - A NEW ANTIFUNGAL COMPOUND FROM SORANGIUM-CELLULOSUM (MYXOBACTERIA) - PRODUCTION, PHYSICOCHEMICAL, AND BIOLOGICAL PROPERTIES [J].
GERTH, K ;
SCHUMMER, D ;
HOFLE, G ;
IRSCHIK, H ;
REICHENBACH, H .
JOURNAL OF ANTIBIOTICS, 1995, 48 (09) :973-976
[6]   LEPTOMYCIN-A AND LEPTOMYCIN-B NEW ANTI-FUNGAL ANTIBIOTICS .1. TAXONOMY OF THE PRODUCING STRAIN AND THEIR FERMENTATION, PURIFICATION AND CHARACTERIZATION [J].
HAMAMOTO, T ;
GUNJI, S ;
TSUJI, H ;
BEPPU, T .
JOURNAL OF ANTIBIOTICS, 1983, 36 (06) :639-645
[7]   LEPTOMYCIN-A AND LEPTOMYCIN-B NEW ANTI-FUNGAL ANTIBIOTICS .2. STRUCTURE ELUCIDATION [J].
HAMAMOTO, T ;
SETO, H ;
BEPPU, T .
JOURNAL OF ANTIBIOTICS, 1983, 36 (06) :646-650
[8]   ANGUINOMYCIN-C AND ANGUINOMYCIN-D, NEW ANTITUMOR ANTIBIOTICS WITH SELECTIVE CYTOTOXICITY AGAINST TRANSFORMED-CELLS [J].
HAYAKAWA, Y ;
SOHDA, K ;
SHINYA, K ;
HIDAKA, T ;
SETO, H .
JOURNAL OF ANTIBIOTICS, 1995, 48 (09) :954-961
[9]   A NEW ANTIBIOTIC, STRUCTURALLY RELATED TO LEPTOMYCIN-A, FLATTENS THE MORPHOLOGY OF V-RAS(TS)NRK CELLS [J].
HOSOKAWA, N ;
IINUMA, H ;
NAGANAWA, H ;
HAMADA, M ;
TAKEUCHI, T ;
ITOH, T ;
HORI, M .
JOURNAL OF ANTIBIOTICS, 1993, 46 (04) :676-678
[10]   Understanding and controlling the cell cycle with natural products [J].
Hung, DT ;
Jamison, TF ;
Schreiber, SL .
CHEMISTRY & BIOLOGY, 1996, 3 (08) :623-639