Cu-mediated enamide formation in the total synthesis of complex peptide natural products

被引：119
作者：
Kuranaga, Takefumi [1 ]
Sesoko, Yusuke [1 ]
Inoue, Masayuki [1 ]
机构：
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
来源：
NATURAL PRODUCT REPORTS | 2014年 / 31卷 / 04期
关键词：
NUCLEOSIDE ANTIBIOTIC MUREIDOMYCIN; PSEUDOMONAS-AERUGINOSA ACTIVITY; SPHEROPLAST FORMING ACTIVITY; WADSWORTH-EMMONS REACTION; BRIDGED NUCLEIC-ACID; DEHYDROAMINO ACIDS; AMINO-ACIDS; STEREOCHEMICAL ASSIGNMENT; CYCLOPEPTIDE ALKALOIDS; ETHYL (DIARYLPHOSPHONO)ACETATES;
D O I：
10.1039/c3np70103d
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Cu-mediated C(sp(2))-N bond formation has received intense interest recently, and has been applied to the total synthesis of a wide variety of structurally complex natural products. This review covers the synthetic assembly of peptide natural products in which Cu-mediated enamide formation is the key transformation. The total syntheses of cyclopeptide alkaloids, pacidamycin D, and yaku'amide A exemplify the versatility of the Cu-catalyzed cross-coupling reaction in comparison to other synthetic methods.
引用
收藏
页码：514 / 532
页数：19
相关论文
共 131 条
  • [1] STRUCTURE OF THIOSTREPTON
    ANDERSON, B
    CROWFOOT.D
    VISWAMIT.MA
    [J]. NATURE, 1970, 225 (5229) : 233 - &
  • [2] Z-selective Horner-Wadsworth-Emmons reaction of ethyl (diarylphosphono)acetates using sodium iodide and DBU
    Ando, K
    Oishi, T
    Hirama, M
    Ohno, H
    Ibuka, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) : 4745 - 4749
  • [3] Z-selective Horner-Wadsworth-Emmons reaction of α-substituted ethyl (diarylphosphono)acetates with aldehydes
    Ando, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) : 8411 - 8416
  • [4] Highly selective synthesis of Z-unsaturated esters by using new Horner-Emmons reagents, ethyl (diarylphosphono)acetates
    Ando, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) : 1934 - 1939
  • [5] SULFURANES .6. REACTIONS INVOLVING ALKOXY LIGANDS OF DIALKOXYDIARYLSULFURANES - FORMATION OF OLEFINS AND ETHERS
    ARHART, RJ
    MARTIN, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (14) : 5003 - &
  • [6] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES
    BAL, BS
    CHILDERS, WE
    PINNICK, HW
    [J]. TETRAHEDRON, 1981, 37 (11) : 2091 - 2096
  • [7] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS
    BARTON, DHR
    MCCOMBIE, SW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16): : 1574 - 1585
  • [8] Sequential N-acylamide methylenation-enamide ring-closing metathesis:: Construction of benzo-fused nitrogen heterocycles
    Bennasar, M. Lluisa
    Roca, Tomas
    Monerris, Manuel
    Garcia-Diaz, Davinia
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18) : 7028 - 7034
  • [9] α,β-dehydroamino acids
    Bonauer, C
    Walenzyk, T
    König, B
    [J]. SYNTHESIS-STUTTGART, 2006, (01): : 1 - 20
  • [10] Synthetic dihydropacidamycin antibiotics: A modified spectrum of activity for the pacidamycin class
    Boojamra, CG
    Lemoine, RC
    Blais, J
    Vernier, NG
    Stein, KA
    Magon, A
    Chamberland, S
    Hecker, SJ
    Lee, VJ
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (19) : 3305 - 3309
12345678910