Formal Total Synthesis of Actinoranone and Asymmetric Synthesis of Labda-7,13-(E)-dien-15-ol

被引:13
作者
Novaes, Luiz F. T. [1 ]
Pastre, Julio C. [1 ]
机构
[1] Univ Campinas UNICAMP, Inst Chem, POB 6154, BR-13084971 Campinas, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
STEREOCHEMICAL REVISION; STRUCTURE ELUCIDATION; CHEMICAL-SYNTHESIS; NATURAL-PRODUCTS; DESIGN; DERIVATIVES;
D O I
10.1021/acs.orglett.7b01287
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses of the polyketide terpenoid fragments of actinoranone are reported in a concise fashion, relying on catalytic methods. Minimization on the use of protecting groqps: and redox reactions allowed the synthesis of the carbon backbone of actinoranone in 20 steps (11 steps for LLS). The asymmetric Synthesis of labda-7,13-(E)-dien-15-ol is also disclosed.
引用
收藏
页码:3163 / 3166
页数:4
相关论文
共 27 条
  • [1] A new goniothalamin N-acylated aza-derivative strongly downregulates mediators of signaling transduction associated with pancreatic cancer aggressiveness
    Barcelos, Rosimeire Coura
    Pelizzaro-Rocha, Karin Juliane
    Pastre, Julio Cezar
    Dias, Marina Pereira
    Ferreira-Halder, Carmen Verissima
    Aloise Pilli, Rona Ido
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 87 : 745 - 758
  • [2] Design and Synthesis of N-Acylated Aza-Goniothalamin Derivatives and Evaluation of Their in vitro and in vivo Antitumor Activity
    Barcelos, Rosimeire Coura
    Pastre, Julio Cezar
    Vendramini-Costa, Debora Barbosa
    Caixeta, Vanessa
    Longato, Giovanna Barbarini
    Monteiro, Paula Araujo
    de Carvalho, Joao Ernesto
    Pilli, Ronaldo Aloise
    [J]. CHEMMEDCHEM, 2014, 9 (12) : 2725 - 2743
  • [3] Redox Economy in Organic Synthesis
    Burns, Noah Z.
    Baran, Phil S.
    Hoffmann, Reinhard W.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) : 2854 - 2867
  • [4] Coibacins A and B: Total Synthesis and Stereochemical Revision
    Carneiro, Vania M. T.
    Avila, Carolina M.
    Balunas, Marcy J.
    Gerwick, William H.
    Pilli, Ronaldo A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (02) : 630 - 642
  • [5] A general model for selectivity in olefin cross metathesis
    Chatterjee, AK
    Choi, TL
    Sanders, DP
    Grubbs, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) : 11360 - 11370
  • [6] Capturing Biological Activity in Natural Product Fragments by Chemical Synthesis
    Crane, Erika A.
    Gademann, Karl
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (12) : 3882 - 3902
  • [7] An approach to furolabdanes and their photooxidation derivatives from R-(+)-sclareolide
    de la Torre, MC
    García, I
    Sierra, MA
    [J]. JOURNAL OF NATURAL PRODUCTS, 2002, 65 (05): : 661 - 668
  • [8] 2-Nitropyrrole cross-coupling enables a second generation synthesis of the heronapyrrole antibiotic natural product family
    Ding, Xiao-Bo
    Furkert, Daniel P.
    Brimble, Margaret A.
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (85) : 12638 - 12641
  • [9] Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination
    Garza, Victoria J.
    Krische, Michael J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (11) : 3655 - 3658
  • [10] Total Synthesis and Stereochemical Assignment of Actinoranone
    Guo, Yi-an
    Zhao, Meng
    Xu, Zhengshuang
    Ye, Tao
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (15) : 3572 - 3576