Synthesis of spiroketal fragment of ossamycin via Prins cyclization

被引：7
|
作者：
Yadav, J. S. [1 ]
Rahman, Md. Ataur [1 ]
Reddy, N. Mallikarjuna [1 ]
Prasad, A. R. [1 ]
机构：
[1] CSIR Indian Inst Chem Technol, Ctr Semiochem, Acad Sci & Innovat Res AcSIR, Hyderabad 500007, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 02期
关键词：
Natural products; Antitumour antibiotic; Prins cyclization; Reductive opening; Spiroketals; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; REDUCTIVE CLEAVAGE; CYTOVARICIN; OLIGOMYCIN; SEGMENT;
D O I：
10.1016/j.tetlet.2014.11.097
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An asymmetric synthesis of spiroketal fragment of an antitumour antibiotic, ossamycin is described. Coupling of aldehyde and alkyne fragments followed by spiroketalization has afforded the spiroketal sub unit of ossamycin. Both the sub targets were constructed via Prins cyclization. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：365 / 367
页数：3
相关论文
共 50 条
  • [1] Synthesis of tetrahydropyrans and related heterocycles via prins cyclization; extension to aza-prins cyclization
    Olier, Clarisse
    Kaafarani, Mustapha
    Gastaldi, Stephane
    Bertrand, Michele P.
    TETRAHEDRON, 2010, 66 (02) : 413 - 445
  • [2] Structure of the spiroketal-macrolide ossamycin
    Kirst, HA
    Mynderse, JS
    Martin, JW
    Baker, PJ
    Paschal, JW
    Steiner, JLR
    Lobkovsky, E
    Clardy, J
    JOURNAL OF ANTIBIOTICS, 1996, 49 (02): : 162 - 167
  • [3] Stereoselective Total Synthesis of Obolactone via Prins Cyclization
    Sabitha, Gowravaram
    Prasad, M. Nagendra
    Shankaraiah, K.
    Yadav, Jhillu S.
    SYNTHESIS-STUTTGART, 2010, (07): : 1171 - 1175
  • [4] Synthesis of the Spiroketal Fragment of (-)-Ushikulide A
    Yadav, Jhillu S.
    Reddy, N. Mallikarjuna
    Rahman, Md. Ataur
    Prasad, Attaluri R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (25) : 5574 - 5581
  • [5] Synthesis of the spiroketal fragment of bistramide A via an exocyclic enol ether
    Tomas, Loic
    Gueyrard, David
    Goekjian, Peter G.
    TETRAHEDRON LETTERS, 2010, 51 (35) : 4599 - 4601
  • [6] Synthesis of an austrodorane sesquiterpenoid core via a transannular Prins cyclization
    Clarke, Paul A.
    Winn, Joby
    TETRAHEDRON LETTERS, 2011, 52 (13) : 1469 - 1472
  • [7] The Stereoselective Total Synthesis of Aculeatin A and B via Prins Cyclization
    Yadav, J. S.
    Thrimurtulu, N.
    Venkatesh, M.
    Prasad, A. R.
    SYNTHESIS-STUTTGART, 2010, (03): : 431 - 436
  • [8] Stereoselective Total Synthesis of Rhoiptelol B via Prins Cyclization
    Yadav, Jhillu S.
    Rahman, Md Ataur
    Reddy, N. Mallikarjuna
    Prasad, Attaluri R.
    Al Ghamdi, Ahmad Al Khazim
    SYNLETT, 2014, 25 (05) : 661 - 664
  • [9] Stereoselective formal synthesis of crocacin C via prins cyclization
    Yadav, J. S.
    Reddy, M. Sridhar
    Rao, P. Purushothama
    Prasad, A. R.
    SYNLETT, 2007, (13) : 2049 - 2052
  • [10] Stereoselective Synthesis of (-)-PF1163A via Prins Cyclization
    Yadav, Jhillu S.
    Venkatesh, M.
    Thrimurtulu, N.
    Prasad, Attaluri R.
    SYNLETT, 2010, (08) : 1255 - 1259
12345