Enantioselective reductive coupling of alkynes and α-keto aldehydes via rhodium-catalyzed hydrogenation:: An approach to bryostatin substructures

被引：38
|
作者：
Cho, CW [1 ]
Krische, MJ [1 ]
机构：
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 05期
关键词：
D O I：
10.1021/ol052976s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Hydrogen-mediated reductive coupling of glyoxal 2 and 1,3-enyne 3 provides (x-hydroxy ketone 4 in 70% yield and 91% enantiomeric excess. Notably, the benzylic ether and diene side chain of 4 remain intact under the conditions of hydrogen-mediated coupling. In four steps, alpha-hydroxy ketone 4 is converted to pyrans 8 and 9, which embody key structural features of the bryostatin recognition domain.
引用
收藏
页码：891 / 894
页数：4
相关论文
共 50 条
  • [21] Reductive aldol coupling of divinyl ketones via rhodium-catalyzed hydrogenation:: syn-diastereoselective construction of β- hydroxyenones
    Han, Soo Bong
    Krische, Michael J.
    ORGANIC LETTERS, 2006, 8 (24) : 5657 - 5660
  • [22] Enantioselective Synthesis of Allylic Sulfones via Rhodium-Catalyzed Direct Hydrosulfonylation of Allenes and Alkynes
    Chang, Chieh-Yu
    Aponick, Aaron
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (25) : 16996 - 17002
  • [23] Rhodium-Catalyzed Enantioselective Spiroannulation of 2-Alkenylphenols with Alkynes
    Zhang Suzhen
    Zhang Wenwen
    Yang Hui
    Gu Qing
    You Shuli
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (08) : 2926 - 2933
  • [24] Enantioselective Rhodium-Catalyzed Dual Ring Expansion of Spirosilabicyclobutane with Alkynes
    Zhu Weike
    Xu Liwen
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (01) : 362 - 364
  • [25] Highly enantioselective rhodium-catalyzed cyclopropenation of terminal alkynes with styryldiazoacetates
    Briones, John F.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [26] Rhodium-Catalyzed Dehydrogenative Coupling of Phenylheteroarenes with Alkynes or Alkenes
    Iitsuka, Tomonori
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (05): : 2804 - 2814
  • [27] Rhodium-Catalyzed Reductive Allylation of Conjugated Aldehydes with Allyl Acetate
    Vasylyev, Maksym
    Alper, Howard
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08): : 2710 - 2713
  • [28] Rhodium-Catalyzed Direct Reductive Amination of Aldehydes and Ketones with Hydrosilanes
    Nogues, Christophe
    Argouarch, Gilles
    CHEMISTRYSELECT, 2020, 5 (27): : 8319 - 8327
  • [29] RHODIUM-CATALYZED HYDROGENATION OF ALDEHYDES BY CARBON MONOXIDE WATER SYSTEM
    WATANABE, Y
    TAKATSUKI, K
    TAKEGAMI, Y
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (APR): : 503 - 503
  • [30] RHODIUM-CATALYZED HYDROGENATION OF ALDEHYDES BY CARBON MONOXIDE WATER SYSTEM
    WATANABE, Y
    TAKATSUKI, K
    TAKEGAMI, Y
    TETRAHEDRON LETTERS, 1978, (36) : 3369 - 3370
12345