Fusicoccin ring system by [4+4] cycloaddition. 2. A model study

被引：11
|
作者：
Sieburth, SM [1 ]
McGee, KF [1 ]
Al-Tel, TH [1 ]
机构：
[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 21期
基金：
美国国家卫生研究院;
关键词：
cycloaddition; natural products; photochemistry; pyridones;
D O I：
10.1016/S0040-4039(99)00671-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthetic approach to fusicoccin A utilizing intramolecular photocycloaddition of tethered 2-pyridones has been completed. This study has led to the first solvent-dependent 2-pyridone photocycloaddition yielding either cis or trans products. Epoxidation of the cis photoproduct is selective for the disubstituted alkene, stabilizes the product, and is properly located for installation of the trans-1,2-diol. Activation of the secondary amide by reaction with an isocyanate led to the reduction of the neopentyl amide carbonyl to a methyl group. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4007 / 4010
页数：4
相关论文
共 50 条
  • [41] “6+2”大于“4+4”
    中学生阅读(高中版)(下半月), 2010, (06) : 61 - 61
  • [42] A 4+3 cycloaddition approach to the spatane ring system
    Harmata, M
    Rashatasakhon, P
    TETRAHEDRON LETTERS, 2001, 42 (33) : 5593 - 5595
  • [43] “6+2”大于“4+4”
    第二课堂(B), 2010, (03) : 31 - 32
  • [44] Computational Study of a Model System of Enzyme-Mediated [4+2] Cycloaddition Reaction
    Gordeev, Evgeniy G.
    Ananikov, Valentine P.
    PLOS ONE, 2015, 10 (04):
  • [45] Intermolecular [4+4] cycloaddition in 2-pyridone mixtures: Complex cyclooctanes from simple aromatic compounds.
    Rucando, D
    Sieburth, SM
    Lin, CH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U68 - U68
  • [46] Supramolecular Rh6 catalytic system promoting directed [4+4] cycloaddition reaction of anthracene under UV irradiation
    Dang, Li-Long
    Li, Ting-Ting
    Zhao, Chen-Chen
    Zhang, Ting-Ting
    Ye, Xiao-Yu
    Sun, Xiao-Tian
    Wang, Hua-Rui
    Ma, Lu-Fang
    JOURNAL OF SOLID STATE CHEMISTRY, 2022, 306
  • [47] Volume Change during Thermal [4+4] Cycloaddition of [2.2] (9,10)Anthracenophane
    Slepetz, Brad
    Kertesz, Miklos
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (37) : 13720 - 13727
  • [48] A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy Towards Oxazocine Scaffolds
    Scuiller, Anais
    Liu, Xueyang
    Cordier, Marie
    Garrec, Julian
    Archambeau, Alexis
    SYNLETT, 2021, 32 (10) : 981 - 986
  • [49] Construction of eight-membered carbocycles by palladium-catalyzed [4+4] cycloaddition of vinylallenes
    Murakami, M
    Itami, K
    Ito, Y
    SYNLETT, 1999, : 951 - 953
  • [50] Diastereocontrol in [4+4]-photocycloadditions of pyran-2-ones: effect of ring substituents and chiral ketal
    Li, Lei
    Bender, John A.
    West, F. G.
    TETRAHEDRON LETTERS, 2009, 50 (11) : 1188 - 1192
12345