Enantioselective Total Synthesis of (-)-Clavosolide A and B

被引:10
|
作者
Son, Jung Beom [1 ]
Kim, Si Nae [1 ]
Kim, Na Yeong [1 ]
Hwang, Min-ho [1 ]
Lee, Wonsun [1 ]
Lee, Duck Hyung [1 ]
机构
[1] Sogang Univ, Dept Chem, Seoul 121742, South Korea
关键词
Enantioselective total synthesis; Clavosolide A; Clavosolide B; MARINE MACROLIDE SYNTHESIS; ALDOL REACTIONS; ASYMMETRIC-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; SELECTIVE REDUCTIONS; ALLYLIC ALCOHOLS; ALKYL-HALIDES; GLYCOSIDES; CYCLOPROPANATION; ANALOGS;
D O I
10.5012/bkcs.2010.31.03.653
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantioselective total synthesis of (-)-clavosolide A and B was reported in full including the synthesis of proposed structure of (-)-clavosoldie A (1), revised structure of (-)-clavosoldie A (5), and revised structure of (-)-clavosoldie B (6). The relative and absolute stereochemistries of the natural products were confirmed unambiguously by comparing the optical rotation values and H-1 and C-13 NMR spectra of them.
引用
收藏
页码:653 / 663
页数:11
相关论文
共 50 条
  • [1] Enantioselective total synthesis of (-)-clavosolide B
    Son, Jung Beom
    Hwang, Min-ho
    Lee, Wonsun
    Lee, Duck-Hyung
    ORGANIC LETTERS, 2007, 9 (20) : 3897 - 3900
  • [2] Total synthesis of clavosolide A
    Chakraborty, Tushar Kanti
    Reddy, Vakiti Ramkrishna
    Gajula, Praveen Kumar
    TETRAHEDRON, 2008, 64 (22) : 5162 - 5167
  • [3] Total synthesis of (-)-clavosolide A
    Chakraborty, Tushar Kanti
    Reddy, Vakiti Ramkrishna
    Chattopadhyay, Anut Kumar
    TETRAHEDRON LETTERS, 2006, 47 (42) : 7435 - 7438
  • [4] Towards the total synthesis of clavosolide A
    Yakambram, Pedduri
    Puranik, Vedavati G.
    Gurjar, Mukund K.
    TETRAHEDRON LETTERS, 2006, 47 (22) : 3781 - 3783
  • [5] Total synthesis of the marine natural product (-)-clavosolide A
    Barry, Conor S.
    Elsworth, Jon D.
    Seden, Peter T.
    Bushby, Nick
    Harding, John R.
    Alder, Roger W.
    Willis, Christine L.
    ORGANIC LETTERS, 2006, 8 (15) : 3319 - 3322
  • [6] Total synthesis of the marine metabolite (-)-clavosolide D
    Seden, Peter T.
    Charmant, Jonathan P. H.
    Willis, Christine L.
    ORGANIC LETTERS, 2008, 10 (08) : 1637 - 1640
  • [7] Enantioselective total synthesis of (+)-cylindricine B
    Dukes, Dallas M.
    Atanassov, Victor K.
    Smith, Joel M.
    CHEMICAL SCIENCE, 2024, 15 (40) : 16554 - 16558
  • [8] Enantioselective total synthesis of cineromycin B
    Takahashi, T
    Watanabe, H
    Kitahara, T
    TETRAHEDRON LETTERS, 2003, 44 (51) : 9219 - 9222
  • [9] Enantioselective Total Synthesis of (+)-Nocardioazine B
    Shen, Xianfu
    Zhao, Jingfeng
    Xi, Yongkai
    Chen, Wen
    Zhou, Yongyun
    Yang, Xiaodong
    Zhang, Hongbin
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (23): : 14507 - 14517
  • [10] Enantioselective total synthesis of salvileucalin B
    Nani, Roger
    Levin, Sergiy
    Reisman, Sarah
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241