A stereoselective synthesis of a 2-functionalized-methyl-1β-methylcarbapenem key intermediate via decarboxylation

被引:8
|
作者
Choi, WB [1 ]
Lee, J [1 ]
Lynch, JE [1 ]
Volante, RP [1 ]
Reider, PJ [1 ]
Reamer, RA [1 ]
机构
[1] Merck Res Labs, Rahway, NJ 07065 USA
关键词
D O I
10.1039/a804125c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient synthesis of a key intermediate 2a for the synthesis of 2-functionalized methyl-1 beta-methylcarbapenem antibiotics 1 has been realized via a stereoselective decarboxylation reaction.
引用
收藏
页码:1817 / 1818
页数:2
相关论文
共 50 条
  • [41] Tetralithiated Tetraazaperopyrene as a Key Intermediate for the Synthesis of Functionalized Derivatives
    Hahn, Lena
    Wadepohl, Hubert
    Gade, Lutz H.
    ORGANIC LETTERS, 2015, 17 (09) : 2266 - 2269
  • [42] A 3-COMPONENT COUPLING APPROACH TO A CHIRAL 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE
    TSUKADA, N
    SHIMADA, T
    GYOUNG, YS
    ASAO, N
    YAMAMOTO, Y
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01): : 143 - 148
  • [43] Stereoselective Total Synthesis of (+)-Casuarine via a Functionalized Pyrrolidine
    Myeong, In-Soo
    Ham, Won-Hun
    SYNTHESIS-STUTTGART, 2022, 54 (10): : 2473 - 2479
  • [44] Stereoselective synthesis of β-functionalized α-aminophosphonates via aziridinium ions
    Piotrowska, DG
    Wróblewski, AE
    TETRAHEDRON, 2003, 59 (42) : 8405 - 8410
  • [45] Stereoselective synthesis of a candoxatril intermediate via asymmetric hydrogenation
    Challenger, S
    Derrick, A
    Mason, CP
    Silk, TV
    TETRAHEDRON LETTERS, 1999, 40 (11) : 2187 - 2190
  • [46] A STEREOCONTROLLED SYNTHESIS OF AN IMPORTANT INTERMEDIATE FOR THE PREPARATION OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS
    FUENTES, LM
    SHINKAI, I
    KING, A
    PURICK, R
    REAMER, RA
    SCHMITT, SM
    CAMA, L
    CHRISTENSEN, BG
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12): : 2563 - 2567
  • [47] SYNTHETIC STUDIES ON (+)-APLASMOMYCIN .2. STEREOSELECTIVE SYNTHESIS OF COREY KEY INTERMEDIATE, A FORMAL TOTAL SYNTHESIS
    NAKATA, T
    SAITO, K
    OISHI, T
    TETRAHEDRON LETTERS, 1986, 27 (52) : 6345 - 6348
  • [48] Efficient Stereoselective Synthesis of a Key Chiral Aldehyde Intermediate in the Synthesis of Picolinamide Fungicides
    Li, Fangzheng
    Good, Steffen
    Tulchinsky, Michael L.
    Whiteker, Gregory T.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (10) : 2253 - 2260
  • [49] Regio- and stereoselective synthesis of key 1-methyl carbapenem intermediates via hydroformylation using a zwitterionic rhodium catalyst
    Park, HS
    Alberico, E
    Alper, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (50) : 11697 - 11703
  • [50] Stereoselective facile synthesis of 2′-spiro pyrimidine pyranonucleosides via their key intermediate 2′-C-cyano analogues. Evaluation of their bioactivity
    Kiritsis, Christos
    Manta, Stella
    Dimopoulou, Athina
    Parmenopoulou, Vanessa
    Gkizis, Petros
    Balzarini, Jan
    Komiotis, Dimitri
    CARBOHYDRATE RESEARCH, 2014, 383 : 50 - 57