Total synthesis and absolute configuration of nocardioazine B

被引:40
作者
Wang, Mingzhong [1 ]
Feng, Xiangyang [1 ,2 ]
Cai, Liangzhen [2 ]
Xu, Zhengshuang [1 ,3 ]
Ye, Tao [1 ,3 ]
机构
[1] Univ Town Shenzhen, Peking Univ Shenzhen Grad Sch, Lab Chem Genom, Shenzhen 518055, Peoples R China
[2] E China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China
[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China
关键词
INDOLE ALKALOID ANALOGS; STEREOCONTROLLED SYNTHESIS; TRYPTOPHAN; REASSIGNMENT; CHEMISTRY;
D O I
10.1039/c2cc31025b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first total synthesis of the indole alkaloid nocardioazine B was accomplished in 10 steps with an overall yield of 11.8%, establishing the absolute stereochemistry of the natural product.
引用
收藏
页码:4344 / 4346
页数:3
相关论文
共 35 条
  • [1] CHEMISTRY OF CYCLIC TAUTOMERS OF TRYPTOPHAN - FORMATION OF A QUATERNARY CENTER AT C3A AND TOTAL SYNTHESIS OF THE MARINE ALKALOID (+)-ENT-DEBROMOFLUSTRAMINE-B
    BRUNCKO, M
    CRICH, D
    SAMY, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) : 5543 - 5549
  • [2] SPONTANEOUS DIKETOPIPERAZINE FORMATION VIA END-TO-END CYCLIZATION OF A NONACTIVATED LINEAR TRIPEPTIDE - AN UNUSUAL CHEMICAL-REACTION
    CARPENTER, KA
    WELTROWSKA, C
    WILKES, BC
    SCHMIDT, R
    SCHILLER, PW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) : 8450 - 8458
  • [3] Towards the stereochemical assignment of natural lydiamycin A
    Chen, Bo
    Dai, Lu
    Zhang, Hui
    Tan, Wenfei
    Xu, Zhengshuang
    Ye, Tao
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (04) : 574 - 576
  • [4] The total syntheses and reassignment of stereochemistry of dragonamide
    Chen, HL
    Feng, YQ
    Xu, ZS
    Xu, ZS
    Ye, T
    [J]. TETRAHEDRON, 2005, 61 (47) : 11132 - 11140
  • [5] Synthesis of the C9-C23 (C9′-C23′) Fragment of the Dimeric Natural Product Rhizopodin
    Chen, Zheng
    Song, Liankai
    Xu, Zhengshuang
    Ye, Tao
    [J]. ORGANIC LETTERS, 2010, 12 (09) : 2036 - 2039
  • [6] The first total synthesis of aeruginosamide
    Chen, ZY
    Ye, T
    [J]. NEW JOURNAL OF CHEMISTRY, 2006, 30 (04) : 518 - 520
  • [7] Total synthesis of cis,cis-ceratospongamide
    Chen, ZY
    Deng, JG
    Ye, T
    [J]. ARKIVOC, 2003, : 268 - 285
  • [8] Chemistry of the hexahydropyrrolo[2,3-b]indoles:: Configuration, conformation, reactivity, and applications in synthesis
    Crich, David
    Banerjee, Abhisek
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (02) : 151 - 161
  • [9] Total synthesis of 5-N-acetylardeemin and amauromine:: Practical routes to potential MDR reversal agents
    Depew, KM
    Marsden, SP
    Zatorska, D
    Zatorski, A
    Bornmann, WG
    Danishefsky, SJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) : 11953 - 11963
  • [10] Cyclopropylazetoindolines as Precursors to C(3)-Quaternary-Substituted Indolines
    Espejo, Vinson R.
    Li, Xi-Bo
    Rainier, Jon D.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) : 8282 - +