Total synthesis of kinamycins C, F, and J

被引:80
作者
Nicolaou, K. C.
Li, Hongming
Nold, Andrea L.
Pappo, Doron
Lenzen, Achim
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
关键词
D O I
10.1021/ja074297d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The kinamycins are a series of naturally occurring compounds endowed with intriguing molecular architectures and potent biological properties, including antibiotic and antitumor activities. These novel diazofluorene-containing compounds defied chemical synthesis since their initial disclosure by Omura et al. in 1970 until the first total synthesis of kinamycin C by Porco et al. in late 2006, and of methyl-kinamycin C by the Kumamoto-Ishihawa group in 2007. We now report our enantioselective total synthesis of kinamycins C, F, and J through a convergent strategy that is both enantioselective and expedient.
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页码:10356 / +
页数:3
相关论文
共 21 条
[1]   Synthesis of indoles via palladium[0]-mediated Ullmann cross-coupling of o-halonitroarenes with α-halo-enones or -enals [J].
Banwell, MG ;
Kelly, BD ;
Kokas, OJ ;
Lupton, DW .
ORGANIC LETTERS, 2003, 5 (14) :2497-2500
[2]  
FURUSAKI A, 1972, ISRAEL J CHEM, V10, P173
[3]   Enantioselective synthesis of a key "A-ring" intermediate for the preparation of 1α-fluoro vitamin D3 analogues [J].
Giuffredi, Guy ;
Bobbio, Carla ;
Gouverneur, Veronique .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5361-5364
[4]   Biosynthesis of the kinamycins [J].
Gould, SJ .
CHEMICAL REVIEWS, 1997, 97 (07) :2499-2509
[5]   REVISED STRUCTURES FOR THE KINAMYCIN ANTIBIOTICS - 5-DIAZOBENZO[B]FLUORENES RATHER THAN BENZO[B]CARBAZOLE CYANAMIDES [J].
GOULD, SJ ;
TAMAYO, N ;
MELVILLE, CR ;
CONE, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :2207-2208
[6]   NEW ANTIBIOTIC, KINAMYCIN - FERMENTATION, ISOLATION, PURIFICATION AND PROPERTIES [J].
HATA, T ;
OMURA, S ;
IWAI, Y ;
NAKAGAWA, A ;
OTANI, M ;
ITO, S ;
MATSUYA, T .
JOURNAL OF ANTIBIOTICS, 1971, 24 (06) :353-&
[7]   Lomaiviticins A and B, potent antitumor antibiotics from Micromonospora lomaivitiensis [J].
He, HY ;
Ding, WD ;
Bernan, VS ;
Richardson, AD ;
Ireland, CM ;
Greenstein, M ;
Ellestad, GA ;
Carter, GT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) :5362-5363
[8]   A NEW ANTIBIOTIC, KINAMYCIN [J].
ITO, S ;
MATSUYA, T ;
OMURA, S ;
OTANI, M ;
NAKAGAWA, A ;
TAKESHIM.H ;
IWAI, Y ;
OHTANI, M ;
HATA, T .
JOURNAL OF ANTIBIOTICS, 1970, 23 (06) :315-&
[9]   Twenty-five years of organic chemistry with diiodosamarium: an overview [J].
Kagan, HB .
TETRAHEDRON, 2003, 59 (52) :10351-10372
[10]   An efficient synthesis of achiral and chiral 1,2,4-triazolium salts: Bench stable precursors for N-heterocyclic carbenes [J].
Kerr, MS ;
de Alaniz, JR ;
Rovis, T .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5725-5728