Total Synthesis of (+)-Clavilactone A and (-)-Clavilactone B by Ring-Opening/Ring-Closing Metathesis

被引:45
|
作者
Takao, Ken-ichi [1 ]
Nanamiya, Ryuki [1 ]
Fukushima, Yuuki [1 ]
Namba, Ayumi [1 ]
Yoshida, Keisuke [1 ]
Tadano, Kin-ichi [1 ]
机构
[1] Keio Univ, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
关键词
REARRANGEMENT METATHESIS; STRUCTURE ELUCIDATION; MOSHER METHOD; ALDEHYDES; CLAVILACTONES; FACILE; BINOL; DIOLS; ACID;
D O I
10.1021/ol4027842
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective total synthesis of natural enantiomers of clavilactones A and B has been achieved. A key feature of the synthesis is the use of a ring-opening/ring-closing metathesis, which allows the one-pot transformation of a strained cyclobutenecarboxylate into a gamma-butenolide.
引用
收藏
页码:5582 / 5585
页数:4
相关论文
共 50 条
  • [41] Synthesis of bicyclic nucleosides by ring-closing metathesis
    Ravn, J
    Nielsen, P
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (09): : 985 - 993
  • [42] Synthesis of cyclic peptidosulfonamides by ring-closing metathesis
    Brouwer, AJ
    Liskamp, RMJ
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11): : 3662 - 3668
  • [43] Synthesis of Azaheterocyclic Vinylphosphonates by Ring-Closing Metathesis
    Garzon, Cecile
    Attolini, Mireille
    Maffei, Michel
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (18) : 3653 - 3657
  • [44] Ring-closing metathesis for the synthesis of a molecular gyrotop
    Setaka, Wataru
    Higa, Sayaka
    Yamaguchi, Kentaro
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (21) : 3354 - 3357
  • [45] Synthesis of cyclic sulfones by ring-closing metathesis
    Yao, QW
    ORGANIC LETTERS, 2002, 4 (03) : 427 - 430
  • [46] A ring-closing metathesis approach for the synthesis of (±)-pregabalin
    Bobade, Vivek D.
    Mhaske, Pravin C.
    Vadgaonkar, Kamlesh S.
    Shelke, Shivaji H.
    MONATSHEFTE FUR CHEMIE, 2012, 143 (05): : 847 - 851
  • [47] Concise total synthesis of (-)-muricatacin by tandem ring-closing/cross metathesis
    Quinn, KJ
    Isaacs, AK
    Arvary, RA
    ORGANIC LETTERS, 2004, 6 (23) : 4143 - 4145
  • [48] Tandem ring-closing metathesis/isomerization reactions for the total synthesis of violacein
    Petersen, Mette T.
    Nielsen, Thomas E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [49] Ring-closing metathesis mediated total synthesis of microcarpalide and herbarumin III
    Gurjar, MK
    Nagaprasad, R
    Ramana, CV
    Karmakar, S
    Mohapatra, DK
    ARKIVOC, 2005, : 237 - 257
  • [50] Synthesis of cyclitols via ring-closing metathesis
    Kornienko, A
    d'Alarcao, M
    TETRAHEDRON-ASYMMETRY, 1999, 10 (05) : 827 - 829