Stereospecificity in Intramolecular Photoredox Reactions of Naphthoquinones: Enantioselective Total Synthesis of (-)-Spiroxin C

被引:39
作者
Ando, Yoshio [1 ]
Hanaki, Atsuko [1 ]
Sasaki, Ryota [1 ]
Ohmori, Ken [1 ]
Suzuki, Keisuke [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, 2-12-1 O Okayama, Tokyo 1528551, Japan
关键词
naphthoquinones; photochemistry; redox reactions; stereospecificity; total synthesis; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; ASYMMETRIC TRANSFER HYDROGENATION; KETONES; CHIRALITY; MEMORY; DEHYDROGENATION; CONVERSION; SPIROXINS; ALDEHYDES; ALCOHOLS;
D O I
10.1002/anie.201705562
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Intramolecular photoredox reactions of naphthoquinone derivatives were found to proceed in a stereospecific manner. This method was used as a basis for the enantioselective total synthesis of (-)-spiroxin C.
引用
收藏
页码:11460 / 11465
页数:6
相关论文
共 39 条
  • [1] Intramolecular Photoredox Reaction of Naphthoquinone Derivatives
    Ando, Yoshio
    Matsumoto, Takashi
    Suzuki, Keisuke
    [J]. SYNLETT, 2017, 28 (09) : 1040 - 1045
  • [2] [Anonymous], 2002, Angew. Chem.
  • [3] TRANSFORMATION OF A METHOXY- INTO A METHYLENEDIOXY-GROUP
    BALDWIN, JE
    BROWN, JE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (04): : 167 - &
  • [4] DEHYDROGENATION OF STEROIDAL AND TRITERPENOID KETONES USING BENZENESELENINIC ANHYDRIDE
    BARTON, DHR
    LESTER, DJ
    LEY, SV
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (10): : 2209 - 2212
  • [5] Total syntheses of (±)-preussomerins G and I
    Chi, S
    Heathcock, CH
    [J]. ORGANIC LETTERS, 1999, 1 (01) : 3 - 5
  • [6] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
    DESS, DB
    MARTIN, JC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 4155 - 4156
  • [7] Eliel E.L., 1994, STEREOCHEMISTRY ORGA, P1119
  • [8] NATURALLY-OCCURRING QUINONES .27. SESQUITERPENOID QUINONES AND RELATED-COMPOUNDS FROM HIBISCUS-ELATUS - CRYSTAL-STRUCTURE OF HIBISCONE-C (GMELOFURAN)
    FERREIRA, MA
    KING, TJ
    ALI, S
    THOMSON, RH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (01): : 249 - 256
  • [9] Fuji K, 1998, CHEM-EUR J, V4, P373, DOI 10.1002/(SICI)1521-3765(19980310)4:3<373::AID-CHEM373>3.0.CO
  • [10] 2-O