An approach to the synthesis of the benzo[b]fluorene core of the kinamycins by an arylalkyne-allene cycloaddition

被引:34
作者
deFrutos, O [1 ]
Echavarren, AM [1 ]
机构
[1] UNIV AUTONOMA MADRID, DEPT QUIM ORGAN, E-28049 MADRID, SPAIN
关键词
D O I
10.1016/S0040-4039(97)10053-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cyclization of an arylalkyne to an allene followed by ring closure was applied for the ready construction of the tetracyclic core of the kinamycin family of antibiotics. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7941 / 7942
页数:2
相关论文
共 17 条
[1]   CYSFLUORETIN, A NEW INHIBITOR OF GLUTATHIONE-S-TRANSFERASE, PRODUCED BY STREPTOMYCES SP MI384-DF12 [J].
AOYAMA, T ;
ZHAO, WJ ;
KOJIMA, F ;
MURAOKA, Y ;
NAGANAWA, H ;
TAKEUCHI, T ;
AOYAGI, T .
JOURNAL OF ANTIBIOTICS, 1993, 46 (09) :1471-1474
[2]   Seongomycin: A new sulfur-containing benzo[b]fluorene derived from genes clustered with those for kinamycin biosynthesis [J].
Carney, JR ;
Hong, ST ;
Gould, SJ .
TETRAHEDRON LETTERS, 1997, 38 (18) :3139-3142
[3]  
FRUTOS O, 1996, TETRAHEDRON LETT, V37, P8953
[4]  
GARCIA JG, 1995, TETRAHEDRON LETT, V36, P7391
[5]  
GILLMANN T, 1995, SYNLETT, P1257
[6]   Kinamycin biosynthesis. Synthesis, isolation, and incorporation of stealthin C, an aminobenzo[b]fluorene [J].
Gould, SJ ;
Melville, CR ;
Cone, MC ;
Chen, J ;
Carney, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :320-324
[7]   Total syntheses of O-4,O-9-dimethyl stealthins A and C [J].
Koyama, H ;
Kamikawa, T .
TETRAHEDRON LETTERS, 1997, 38 (22) :3973-3976
[8]   THERMAL GENERATION OF ALPHA,3-DEHYDROTOLUENE FROM (Z)-1,2,4-HEPTATRIEN-6-YNE [J].
MYERS, AG ;
KUO, EY ;
FINNEY, NS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8057-8059
[9]   BIRADICAL FORMATION FROM ACYCLIC CONJUGATED ENEYNE-ALLENE SYSTEM RELATED TO NEOCARZINOSTATIN AND ESPERAMICIN-CALICHEMICIN [J].
NAGATA, R ;
YAMANAKA, H ;
OKAZAKI, E ;
SAITO, I .
TETRAHEDRON LETTERS, 1989, 30 (37) :4995-4998
[10]   Thermal and electron transfer induced reactions of enediynes and enyne allenes .3. Intramolecular formal Diels-Alder reaction in enyne allenes. A new synthetic route to benzofluorenes and indeno[1,2-g]quinolines [J].
Schmittel, M ;
Strittmatter, M ;
Vollmann, K ;
Kiau, S .
TETRAHEDRON LETTERS, 1996, 37 (07) :999-1002