First synthesis of an amythiamicin pyridine cluster

被引:30
作者
Bagley, MC
Dale, JW
Jenkins, RL
Bower, J
机构
[1] Cardiff Univ, Sch Chem, Cardiff CF10 3TB, S Glam, Wales
[2] Vernalis, Cambridge CB1 6GB, England
关键词
D O I
10.1039/b310944e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The pyridine-containing central domain of the amythiamicin group of thiopeptide antibiotics is prepared in protected form in 9 steps, 93% ee and 18% overall yield from (S)-2-[1-(tert-butoxycarbonylamino)-2-methylpropylithiazole-4-carboxylic acid by Michael addition-cyclodehydration of a 2-(2-thiazolyl)enamine and 1-(2-thiazolyl)propynone.
引用
收藏
页码:102 / 103
页数:2
相关论文
共 14 条
  • [1] REINVESTIGATION OF A MODIFIED HANTZSCH THIAZOLE SYNTHESIS
    AGUILAR, E
    MEYERS, AI
    [J]. TETRAHEDRON LETTERS, 1994, 35 (16) : 2473 - 2476
  • [2] One-pot synthesis of pyridines or pyrimidines by tandem oxidation-heteroannulation of propargylic alcohols
    Bagley, MC
    Hughes, DD
    Sabo, HM
    Taylor, PH
    Xiong, X
    [J]. SYNLETT, 2003, (10) : 1443 - 1446
  • [3] A new one-step synthesis of pyridines under microwave-assisted conditions
    Bagley, MC
    Lunn, R
    Xiong, X
    [J]. TETRAHEDRON LETTERS, 2002, 43 (46) : 8331 - 8334
  • [4] A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines
    Bagley, MC
    Dale, JW
    Bower, J
    [J]. CHEMICAL COMMUNICATIONS, 2002, (16) : 1682 - 1683
  • [5] Synthesis of tetrasubstituted pyridines by the acid-catalysed Bohlmann-Rahtz reaction
    Bagley, MC
    Brace, C
    Dale, JW
    Ohnesorge, M
    Phillips, NG
    Xiong, X
    Bower, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (14): : 1663 - 1671
  • [6] Bagley MC, 2001, SYNLETT, P1523
  • [7] Total synthesis of the thiopeptide promothiocin A
    Bagley, MC
    Bashford, KE
    Hesketh, CL
    Moody, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) : 3301 - 3313
  • [8] Synthesis of the Bycroft-Gowland structure of micrococcin P1
    Ciufolini, MA
    Shen, YC
    [J]. ORGANIC LETTERS, 1999, 1 (11) : 1843 - 1846
  • [9] The first synthesis of promothiocin A
    Moody, CJ
    Bagley, MC
    [J]. CHEMICAL COMMUNICATIONS, 1998, (18) : 2049 - 2050
  • [10] NOVEL ANTIBIOTICS, AMYTHIAMICINS .2. STRUCTURE ELUCIDATION OF AMYTHIAMICIN-D
    SHIMANAKA, K
    TAKAHASHI, Y
    IINUMA, H
    NAGANAWA, H
    TAKEUCHI, T
    [J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (10) : 1145 - 1152