STEREOSELECTIVE APPROACH TOWARD OPHIODILACTONES BASED ON AN INTRAMOLECULAR [2+2] CYCLOADDITION REACTION

被引：4
|
作者：
Matsubara, Takaaki [1 ]
Ishihara, Jun [1 ]
Hatakeyama, Susumi [1 ]
机构：
[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan
来源：
HETEROCYCLES | 2015年 / 90卷 / 01期
关键词：
Baeyer-Villiger Oxidation; 2+2] Cycloaddition; Ketene; Lactone; Natural Product Synthesis; DIPOLAR APROTIC MEDIA; ALPHA-CYANO ESTERS; BETA-KETO-ESTERS; SYNTHETIC APPLICATIONS; MALONATE ESTERS; DEALKOXYCARBONYLATIONS; ALDEHYDES; CHLORIDE; WATER;
D O I：
10.3987/COM-14-S(K)32
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The highly enantio- and diastereoselective synthesis of a promising precursor of ophiodilactones A and B, tetrameric phenylpropanoids isolated from the ophiuroid Ophiocoma scolopendrina, is described. The synthesis involves an organocatalytic asymmetric Michael reaction, intramolecular [2 + 2] cycloaddition of a ketene to an alkene, Baeyer-Villiger oxidation, and construction of the C2 quaternary center as major transformations.
引用
收藏
页码：405 / 424
页数：20
相关论文
共 50 条
  • [11] INTRAMOLECULAR [2+2] CYCLOADDITION AND SEQUENTIAL RING EXPANSION
    ZHANG, W
    COLLINS, MR
    MAHMOOD, K
    DOWD, P
    TETRAHEDRON LETTERS, 1995, 36 (16) : 2729 - 2732
  • [12] DEVELOPMENT OF AN INTRAMOLECULAR GASSMAN'S [2+2] CYCLOADDITION
    Feltenberger, John B.
    Ko, Changhong
    Deng, Jun
    Ghosh, Sunil K.
    Hsung, Richard P.
    HETEROCYCLES, 2012, 84 (02) : 843 - 878
  • [13] Tandem Vinylogous Aldol and Intramolecular [2+2] Cycloaddition toward Benzocyclobutenes by UV Light Photocatalysis
    Tan, Hong-bo
    Liu, Ying-shan
    Zhou, Jia-ying
    Cao, Man
    Lei, Tong
    Ren, Si-ying
    Lin, Chang-qiu
    Yang, Yi-fan
    Hu, Zhang-liang
    Xu, Zhi-gang
    Tang, Dian-yong
    Chen, Zhong-zhu
    Qu, Xian-you
    ORGANIC LETTERS, 2024, 26 (15) : 3304 - 3309
  • [14] Microwave-assisted intramolecular [2+2] cycloaddition reaction for the rapid and regiospecific synthesis of bicyclomethylenecylcobutene
    Brummond, Kay M.
    Chen, Daitao
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3346 - U3346
  • [15] Ruthenium-Catalyzed (2+2) Intramolecular Cycloaddition of Allenenes
    Gulias, Moises
    Collado, Alba
    Trillo, Beatriz
    Lopez, Fernando
    Onate, Enrique
    Esteruelas, Miguel A.
    Mascarenas, Jose L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) : 7660 - 7663
  • [16] Ruthenium- catalyzed (2+2) intramolecular cycloaddition of allenenes
    Gulias, Moises
    Collado, Alba
    Luis Mascarenas, Jose
    Angel Esteruelas, Miguel
    Seoane, Andres
    Onate, Enrique
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [17] INTRAMOLECULAR PHOTO[2+2]CYCLOADDITION OF 2-ALKENOYLOXYCYCLOHEX-2-ENONES
    IKEDA, M
    TAKAHASHI, M
    UCHINO, T
    TAMURA, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1984, 32 (02) : 538 - 542
  • [18] Stereoselective preparation of methylenecyclobutane-fused angular tetracyclic spiroindolines via photosensitized intramolecular [2+2] cycloaddition with allene
    Arai, Noriyoshi
    Ohkuma, Takeshi
    TETRAHEDRON LETTERS, 2019, 60 (46)
  • [19] [2+2] Carbonylative cycloaddition catalyzed by palladium:: stereoselective synthesis of β-lactams
    Troisi, L
    De Vitis, L
    Granito, C
    Pilat, W
    Pindinelli, E
    TETRAHEDRON, 2004, 60 (32) : 6895 - 6900
  • [20] Stereoselective Construction of Highly Functionalized Azetidines via a [2+2]-Cycloaddition
    Ye, Yang
    Wang, Hua
    Fan, Renhua
    ORGANIC LETTERS, 2010, 12 (12) : 2802 - 2805
12345