Stereoselective total synthesis of (+)-sapinofuranone B

被引:19
|
作者
Yadav, J. S. [1 ]
Mandal, S. S. [1 ]
Reddy, J. S. S. [1 ]
Srihari, P. [1 ]
机构
[1] Indian Inst Chem Technol, Organ Div 1, CSIR, Hyderabad 500607, Andhra Pradesh, India
关键词
GAMMA-LACTONE; ALKYNES; ACID;
D O I
10.1016/j.tet.2011.04.072
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two approaches for the total synthesis of (+)-sapinofuranone B have been described. The first strategy utilizes the methodology developed earlier in our group to get the chiral propargyl alcohol and the second strategy involves generation of threo-1,2-diol derivative by diastereoselective and enantioselective addition of [(Z)-gamma-methoxymethoxyallyl]diisopinocampheylborane onto aldehyde and cross metathesis as the key steps. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4620 / 4627
页数:8
相关论文
共 50 条
  • [21] Stereoselective total synthesis of sporiolide B and attempted synthesis of sporiolide A
    Sridhar, Gattu
    Sharma, Gangavaram V. M.
    SYNTHETIC COMMUNICATIONS, 2016, 46 (04) : 314 - 321
  • [22] First stereoselective total synthesis of ophiocerins B and c
    Yadav, J. S.
    Lakshmi, P. Naga
    Harshavardhan, S. J.
    Reddy, B. V. Subba
    SYNLETT, 2007, (12) : 1945 - 1947
  • [23] Bioinspired First Stereoselective Total Synthesis of Spinosulfate B
    Bokam, Ramesh
    Annam, S. Ch V. Appa Rao
    Yalavarthi, Nageswara Rao
    Gundoju, Narayanarao
    Ponnapalli, Mangala Gowri
    CHEMISTRYSELECT, 2019, 4 (31): : 8911 - 8914
  • [24] Stereoselective Total Synthesis of epi-Phomopsolide B
    Emmadi, Narender Reddy
    Bingi, Chiranjeevi
    Kumar, Chityal Ganesh
    Yedla, Poornachandra
    Atmakur, Krishnaiah
    SYNTHESIS-STUTTGART, 2014, 46 (21): : 2945 - 2950
  • [25] Stereoselective total synthesis of oplopandiol, oploxyne A, and oploxyne B
    Reddy, B. V. Subba
    Rao, R. Nageshwar
    Kumaraswamy, B.
    Yadav, J. S.
    TETRAHEDRON LETTERS, 2014, 55 (33) : 4590 - 4592
  • [26] Stereoselective total synthesis of iso-cladospolide B
    Srihari, P.
    Bhasker, E. Vijaya
    Harshavardhan, S. J.
    Yadav, J. S.
    SYNTHESIS-STUTTGART, 2006, (23): : 4041 - 4045
  • [27] 1,2-Dibromoalkanes into alkynes by elimination reaction under DBU conditions and their application to total synthesis of sapinofuranone B
    Kutsumura, Noriki
    Yokoyama, Tadashi
    Ohgiya, Tadaaki
    Nishiyama, Shigeru
    TETRAHEDRON LETTERS, 2006, 47 (25) : 4133 - 4136
  • [28] Stereoselective total synthesis of synparvolide B and epi-synparvolide A
    Srihari, P.
    Bhasker, E. Vijaya
    Reddy, A. Bal
    Yadav, J. S.
    TETRAHEDRON LETTERS, 2009, 50 (20) : 2420 - 2424
  • [29] 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
  • [30] A stereoselective approach to the angucyclinone antibiotics: A total synthesis of (±)-urdamycinone B
    Osman, Hasnah
    Larsen, David S.
    Muralikrishna, Akkarapalli
    ARABIAN JOURNAL OF CHEMISTRY, 2019, 12 (08) : 2501 - 2512