Formal Total Synthesis of Brevisamide by Using a Tandem Isomerization/C-O and C-C Bond Formation Reaction

被引：5
|
作者：
Banoth, Shivalal [1 ]
Maity, Saurabh [1 ]
Kumar, Sudheer R. [1 ]
Yadav, J. S. [1 ]
Mohapatra, Debendra K. [1 ]
机构：
[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 13期
关键词：
Natural products; Aldol reactions; Chiral auxiliaries; Iodocyclization; Olefination; DINOFLAGELLATE KARENIA-BREVIS; ASYMMETRIC ALDOL ADDITIONS; BREVETOXIN-B; STEREOSELECTIVE-SYNTHESIS; CURTIUS REARRANGEMENT; PTYCHODISCUS-BREVIS; CARBOXYLIC-ACIDS; BICYCLIC CORE; IODOCYCLIZATION; (+)-SORANGICIN;
D O I：
10.1002/ejoc.201600142
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly stereoselective formal total synthesis of brevisamide is described that proceeds through a convergent pathway and utilizes our own tandem isomerization/C-O and C-C bond formation reaction as the key step to construct the trans-2,6-disubstituted dihydropyran ring system. Other significant reactions in this synthesis include an iodolactonization, a Crimmins-modified non-Evans syn aldol reaction, and a Horner-Wadsworth-Emmons olefination.
引用
收藏
页码：2300 / 2307
页数：8
相关论文
共 50 条
  • [1] Stereoselective synthesis of (+)-decarestrictine L using tandem isomerization followed by C-O and C-C bond formation reaction
    Banoth, Shivalal
    Kanikarapu, Suresh
    Yadav, Jhillu S.
    Mohapatra, Debendra K.
    TETRAHEDRON LETTERS, 2016, 57 (39) : 4368 - 4370
  • [2] AN ENANTIOSELECTIVE SYNTHESIS OF N-METHYLFUCOSAMINE VIA TANDEM C-C C-O BOND FORMATION
    SAMES, D
    POLT, R
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16): : 4596 - 4601
  • [3] AN ENANTIOSELECTIVE SYNTHESIS OF N-METHYLFUCOSAMINE VIA TANDEM C-C/C-O BOND FORMATION
    SAMES, D
    POLT, R
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 392 - ORGN
  • [4] NEW METHODS OF C-C AND C-O BOND FORMATION IN THE SYNTHESIS OF CONJUGATED POLYMERS
    KLAPPER, M
    MULLEN, K
    MACROMOLECULAR SYMPOSIA, 1995, 98 : 233 - 246
  • [5] Synthesis of bicyclic lactones via I2-mediated intramolecular tandem C-C/C-O bond formation
    Maejima, Saki
    Osuka, Mai
    Yamaguchi, Eiji
    Itoh, Akichika
    TETRAHEDRON, 2018, 74 (24) : 2985 - 2990
  • [6] One-pot C-C/C-O bond formation: synthesis of spirocyclic lactones
    Niharika, Pedireddi
    Satyanarayana, Gedu
    RSC ADVANCES, 2016, 6 (02): : 837 - 843
  • [7] InIII-Catalysed Tandem C-C and C-O Bond Formation between Phenols and Allylic Acetates
    Vece, Vito
    Ricci, Jeremy
    Poulain-Martini, Sophie
    Nava, Paola
    Carissan, Yannick
    Humbel, Stephane
    Dunach, Elisabet
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (32) : 6239 - 6248
  • [8] New methods for C-C, C-O, and C-N bond formation
    Walsh, Patrick J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [9] Palladium(II)-Catalyzed C-H Bond Activation/C-C and C-O Bond Formation Reaction Cascade: Direct Synthesis of Coumestans
    Neog, Kashmiri
    Borah, Ashwini
    Gogoi, Pranjal
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23): : 11971 - 11977
  • [10] Expedient Synthesis of Functionalized Triarylmethanols through Tandem Formation of Geminal C-C and C-O Bonds
    Tian, Yu
    Sui, Yi
    Gu, Yonghong
    Tian, Shi-Kai
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (18) : 3475 - 3479
12345