The first total synthesis of prianosin B

被引:11
|
作者
Wada, Yasufumi [1 ]
Otani, Kouji [1 ]
Endo, Noriko [1 ]
Harayama, Yu [1 ]
Kamimura, Daigo [1 ]
Yoshida, Masako [1 ]
Fujioka, Hiromichi [1 ]
Kita, Yasuyuki [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
基金
日本学术振兴会;
关键词
HYPERVALENT IODINE(III) REAGENT; SULFUR-CONTAINING ALKALOIDS; EFFICIENT DIRECT SYNTHESIS; METAL-DIENE COMPLEXES; DISCORHABDIN-C; PYRROLOIMINOQUINONE ALKALOIDS; MARINE ALKALOIDS; TOPOISOMERASE-II; MAKALUVAMINE-D; PYRROLOQUINOLINE NUCLEUS;
D O I
10.1016/j.tet.2008.11.051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first asymmetric total synthesis of prianosin B (1) is described. Formation of the 16,17-dehydropyrroloiminoquinone skeleton from the pyrroloiminoquinone unit is a key step in this synthesis. Thus, the detosylation and dehydrogenation reactions of the pyrroloiminoquinone unit are Caused by the presence of a catalytic amount of NaN3. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1059 / 1062
页数:4
相关论文
共 50 条
  • [1] First total synthesis of aerucyclamide B
    Pena, Stella
    Scarone, Laura
    Manta, Eduardo
    Serra, Gloria
    TETRAHEDRON LETTERS, 2013, 54 (22) : 2806 - 2808
  • [2] The First Total Synthesis of Saurufuran B
    Yi Hua YANG
    Chinese Chemical Letters, 2006, (10) : 1287 - 1289
  • [3] The first total synthesis of (+/-)-huperzine B
    Wu, BG
    Bai, DL
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17): : 5978 - 5981
  • [4] First total synthesis of theopederin B
    Nishii, Yoshinori
    Higa, Tsuyoshi
    Takahashi, Shunya
    Nakata, Tadashi
    TETRAHEDRON LETTERS, 2009, 50 (26) : 3597 - 3601
  • [5] First total synthesis of crassostreaxanthin B
    Tode, C
    Yamano, Y
    Ito, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (12): : 1625 - 1626
  • [6] The first total synthesis of sideroxylonal B
    Tatsuta, K
    Tamura, T
    Mase, T
    TETRAHEDRON LETTERS, 1999, 40 (10) : 1925 - 1928
  • [7] The first total synthesis of (±)-herbertenones A and B
    Srikrishna, Adusumilli
    Ravikumar, Ponneri C.
    Krishnan, Hema S.
    SYNTHESIS-STUTTGART, 2008, (10): : 1527 - 1534
  • [8] First total synthesis of (±)hedaol B
    Li, Y
    Lu, B
    Li, CH
    Li, WL
    SYNTHETIC COMMUNICATIONS, 2003, 33 (08) : 1417 - 1423
  • [9] First total synthesis of (-)-sinularianin B
    Ota, Koichiro
    Miyaoka, Hiroaki
    CHEMICAL COMMUNICATIONS, 2013, 49 (74) : 8148 - 8150
  • [10] First total synthesis of (±)-kenusanone B
    Xiao, L
    Tan, WF
    Li, YL
    SYNTHETIC COMMUNICATIONS, 1998, 28 (15) : 2861 - 2869