Enantioselective, Protecting-Group-Free Total Synthesis of Boscartin F

被引：21
作者：
Matsuzawa, Akinobu [1 ]
Shiraiwa, Junya [1 ]
Kasamatsu, Akihiko [1 ]
Sugita, Kazuyuki [1 ]
机构：
[1] Hoshi Univ, Fac Pharmaceut Sci, Dept Synthet Med Chem, Shinagawa Ku, 2-4-41 Ebara, Tokyo 1428501, Japan
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 04期
关键词：
CORAL SINULARIA-FLEXIBILIS; INCENSOLE; METATHESIS; CEMBRANOIDS; CATALYSTS; OLEFINS; OXIDE; RESIN;
D O I：
10.1021/acs.orglett.7b03979
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this work, the protecting-group-free total synthesis and stereochemical assignment of (-)-boscartin F have been reported. The key steps, including Sharpless asymmetric epoxidation, I-2-mediated iodoetherification, aldol reaction, and ring-closing metathesis, allowed for rapid and highly stereoselective access to boscartin F. In addition, single-crystal X-ray crystallographic analysis of the semicarbazone derivative 22 confirmed the stereochemistry of boscartin F.
引用
收藏
页码：1031 / 1033
页数：3
相关论文
共 25 条
  • [1] Three new cembranoid-type diterpenes from Red Sea soft coral Sarcophyton glaucum: Isolation and antiproliferative activity against HepG2 cells
    Al-Lihaibi, Sultan S.
    Alarif, Walled M.
    Abdel-Lateff, Ahmed
    Ayyad, Seif-Eldin N.
    Abdel-Naim, Ashraf B.
    El-Senduny, Fardous F.
    Badria, Farid A.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 81 : 314 - 322
  • [2] SYNTHESIS OF A FUNCTIONALIZED BIS-SPIROACETAL
    BRIMBLE, MA
    WILLIAMS, GM
    BAKER, R
    JAMES, M
    [J]. TETRAHEDRON LETTERS, 1990, 31 (21) : 3043 - 3046
  • [3] STRUCTURE OF INCENSOLE
    CORSANO, S
    NICOLETTI, R
    [J]. TETRAHEDRON, 1967, 23 (04) : 1977 - +
  • [4] Novel cytotoxic cembranoids from the soft coral Sinularia flexibilis
    Duh, CY
    Wang, SK
    Tseng, HK
    Sheu, JH
    Chiang, MY
    [J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (06): : 844 - 847
  • [5] Asymmetric induction in methyl ketone aldol additions to α-alkoxy and α,β-bisalkoxy aldehydes:: A model for acyclic stereocontrol
    Evans, David A.
    Cee, Victor J.
    Siska, Sarah J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) : 9433 - 9441
  • [6] An Umpolung Approach to Alkene Carboamination: Palladium Catalyzed 1,2-Amino-Acylation, -Carboxylation, -Arylation, -Vinylation, and -Alkynylation
    Faulkner, Adele
    Scott, James S.
    Bower, John F.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (22) : 7224 - 7230
  • [7] FORCELLE.ML, 1973, TETRAHEDRON LETT, P3783
  • [8] STRUCTURE OF ISOINCENSOLE-OXIDE
    FORCELLESE, ML
    NICOLETTI, R
    PETROSSI, U
    [J]. TETRAHEDRON, 1972, 28 (02) : 325 - +
  • [9] Intramolecular Condensation via an o-Quinone Methide: Total Synthesis of (±)-Heliol
    Green, Jason C.
    Brown, Eric R.
    Pettus, Thomas R. R.
    [J]. ORGANIC LETTERS, 2012, 14 (12) : 2929 - 2931
  • [10] Structure and properties of constituents in hexane extract of frankincense
    Hasegawa, Toshio
    Kikuchi, Akiko
    Saitoh, Hideki
    Yamada, Hideo
    [J]. JOURNAL OF ESSENTIAL OIL RESEARCH, 2012, 24 (06) : 593 - 598
123