Total Synthesis and Structural Revision of Cephalosporolide J

被引：0
作者：
Ota, Koichiro [1 ]
Kamaike, Kazuo [1 ]
Miyaoka, Hiroaki [1 ]
机构：
[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan
来源：
SYNLETT | 2023年 / 34卷 / 03期
关键词：
cephalosporolide J; polyketide; bicyclo[3; 3; 0]furanolactone; total synthesis; structural revision; MARINE-DERIVED FUNGUS; STYRYL-LACTONES; STEREOSELECTIVE-SYNTHESIS; GONIOFUFURONE; INTERMEDIATE;
D O I：
10.1055/a-1967-1284
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report the first total synthesis of cephalosporo-lide J, which is a deep sea sediment derived polyketide harboring aunique bicyclo[3.3.0]furanolactone moiety. The adopted syntheticstrategy consisted of the alkynylation of gamma-lactone with lithium alkynyl-trifluoroborate followed by a spiroketalization triggered by hydrogena-tion of the triple bond. Through this synthesis, the correct structure ofcephalosporolide J is shown to be that of the 9-epi stereoisomer of thestructure originally proposed.
引用
收藏
页码：271 / 276
页数：6
相关论文
共 45 条
  • [1] STRUCTURES OF THE CEPHALOSPOROLIDES B-F, A GROUP OF C-10 LACTONES FROM CEPHALOSPORIUM-APHIDICOLA
    ACKLAND, MJ
    HANSON, JR
    HITCHCOCK, PB
    RATCLIFFE, AH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (04): : 843 - 847
  • [2] Conformationally constrained goniofufurone mimics as inhibitors of tumour cells growth: Design, synthesis and SAR study
    Benedekovic, Goran
    Francuz, Jovana
    Kovacevic, Ivana
    Popsavin, Mirjana
    Sreco Zelenovic, Bojana
    Kojic, Vesna
    Bogdanovic, Gordana
    Divjakovic, Vladimir
    Popsavin, Velimir
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 82 : 449 - 458
  • [3] Blázquez MA, 1999, PHYTOCHEM ANALYSIS, V10, P161, DOI 10.1002/(SICI)1099-1565(199907/08)10:4<161::AID-PCA453>3.0.CO
  • [4] 2-2
  • [5] A convergent synthesis of the [4.4]-spiroacetal-γ-lactones cephalosporolides E and F
    Brimble, Margaret A.
    Finch, Orla C.
    Heapy, Amanda M.
    Fraser, John D.
    Furkert, Daniel P.
    O'Connor, Patrick D.
    [J]. TETRAHEDRON, 2011, 67 (05) : 995 - 1001
  • [6] IMPROVED HIGHLY EFFICIENT SYNTHESIS OF ALPHA,BETA-ACETYLENIC KETONES - NATURE OF THE INTERMEDIATE FROM THE REACTION OF LITHIUM ACETYLIDE WITH BORON-TRIFLUORIDE ETHERATE
    BROWN, HC
    RACHERLA, US
    SINGH, SM
    [J]. TETRAHEDRON LETTERS, 1984, 25 (23) : 2411 - 2414
  • [7] Enantioselective Synthesis of Spiroacetals via Silver(I)-Promoted Alkylation of Hemiacetals: Total Synthesis of Cephalosporolides E and F
    Chang, Stanley
    Britton, Robert
    [J]. ORGANIC LETTERS, 2012, 14 (23) : 5844 - 5847
  • [8] A concise protecting-group-free synthesis of cephalosporolides E and F
    Chaudhari, Dipali A.
    Kattanguru, Pullaiah
    Fernandes, Rodney A.
    [J]. RSC ADVANCES, 2015, 5 (52): : 42131 - 42134
  • [9] PPAR Modulating Polyketides from a Chinese Plakortis simplex and Clues on the Origin of Their Chemodiversity
    Chianese, Giuseppina
    Yu, Hao-Bing
    Yang, Fan
    Sirignano, Carmina
    Luciano, Paolo
    Han, Bing-Nan
    Khan, Shabana
    Lin, Hou-Wen
    Taglialatela-Scafati, Orazio
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (12) : 5135 - 5143
  • [10] Total Synthesis of Cephalosporolide E via a Tandem Radical/Polar Crossover Reaction. The Use of the Radical Cations under Nonoxidative Conditions in Total Synthesis
    Cortezano-Arellano, Omar
    Quintero, Leticia
    Sartillo-Piscil, Fernando
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (05) : 2601 - 2608
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