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
  • [1] Fusicoccin ring system by [4+4] cycloaddition. Control of diastereoselectivity through hydrogen bonding
    Sieburth, SM
    McGee, KF
    Al-Tel, TH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (03) : 587 - 588
  • [2] The fusicoccin framework by highly diastereoselective photo-[4+4]-cycloaddition.
    Sieburth, SM
    AlTel, TH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 419 - ORGN
  • [3] Diastereoselectivity during 2-pyridone photo-[4+4] cycloaddition. The tribenzylsilyl protecting group
    Sieburth, SM
    Madsen-Duggan, CB
    Zhang, FN
    TETRAHEDRON LETTERS, 2001, 42 (31) : 5155 - 5157
  • [4] Fusicoccin synthesis by intramolecular [4+4] photocycloaddition of 2-pyridones: Stereocontrol of the cycloaddition and elaboration of the pentacyclic product
    McGee, KF
    Al-Tel, TH
    Sieburth, SM
    SYNTHESIS-STUTTGART, 2001, (08): : 1185 - 1196
  • [5] Fusicoccin synthesis by intramolecular [4+4] photocycloaddition of 2-pyridones: Stereocontrol of the cycloaddition and elaboration of the pentacyclic product
    McGee Jr., K.F.
    Al-Tel, T.H.
    Sieburth, S.McN.
    Synthesis, 2001, (08) : 1185 - 1196
  • [6] [4+4] Photocycloaddition of 2-pyridones: Progress towards the total synthesis of Fusicoccin A
    Finn, Paul B.
    Sieburth, Scott McN
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [7] Photo-[4+4]-cycloaddition of enynes
    Kulyk, Svitlana
    Sieburth, Scott McN
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [8] Nickel catalyzed 4+4 cycloaddition of dienes
    Kativhu, Elton
    Greco, George
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [9] Enyne [4+4] Cycloaddition/Oxidation: Ring Contraction via Cyclopropanones and Their Anionic Ring-Opening Reactions
    Kulyk, Svitlana
    Khatri, Buddha B.
    Sieburth, Scott McN.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (01) : 319 - 323
  • [10] Beyond the medium ring: A [4+4] cycloaddition fragmentation synthesis of eleven-membered rings
    Sieburth, SM
    AlTel, TH
    Rucando, D
    TETRAHEDRON LETTERS, 1997, 38 (49) : 8433 - 8434
12345