Efficient and stereoselective synthesis of novel cis 4-substituted proline analogues

被引:15
|
作者
Zhang, JY
Wang, W
Xiong, CY
Hruby, VJ
机构
[1] Novartis Res Fdn, Genom Inst, San Diego, CA 92121 USA
[2] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
关键词
proline; constrained amino acids; alkylation;
D O I
10.1016/S0040-4039(02)02865-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel cis-4-substituted proline analogues were designed and synthesized. Highly stereoselective alkylations at the gamma-position of glutamic ester 2 were achieved, followed by reduction, mesylation, and cyclization to afford the title compounds 1 in good yields and high diastereoselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1413 / 1415
页数:3
相关论文
共 50 条
  • [41] SYNTHESIS OF NEW 4-SUBSTITUTED XANTHOTOXINS
    ELHAMOULY, WS
    ABOULEZZ, AF
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (04): : 373 - 376
  • [42] USEFUL SYNTHESIS OF 4-SUBSTITUTED INDOLES
    PONTICELLO, GS
    BALDWIN, JJ
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22): : 4003 - 4005
  • [43] METHOD FOR SYNTHESIS OF 4-SUBSTITUTED ACETOACETATES
    TROOSTWIJK, CB
    KELLOGG, RM
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (24) : 932 - 933
  • [44] A NEW SYNTHESIS OF 4-SUBSTITUTED COUMARINS
    PATRA, A
    MISRA, SK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1990, 29 (01): : 66 - 69
  • [45] SYNTHESIS AND SOLVOLYSIS OF 4-SUBSTITUTED NORTRICYCLENES
    CHENIER, PJ
    MCCLURE, JR
    GOLEMBESKI, DJ
    JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (22): : 4306 - 4310
  • [46] A NEW SYNTHESIS OF 4-SUBSTITUTED ISOQUINOLINES
    MINTER, DE
    RE, MA
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11): : 2653 - 2655
  • [47] PREPARATION AND PROPERTIES OF SOME 4-SUBSTITUTED ANALOGUES OF CYTOSINE AND DIHYDROCYTOSINE
    JANION, C
    SHUGAR, D
    ACTA BIOCHIMICA POLONICA, 1968, 15 (03) : 261 - &
  • [48] Cyclization of aryllithiums tethered to methylenecycloalkanes:: Stereoselective synthesis of 4α-substituted cis-hexahydrofluorenes
    Bailey, WF
    Daskapan, T
    Rampalli, S
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04): : 1334 - 1338
  • [49] Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides
    El Akri, Khalid
    Bougrin, Khalid
    Balzarini, Jan
    Faraj, Abdesslem
    Benhida, Rachid
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (23) : 6656 - 6659
  • [50] Synthesis and antiproliferative activity of (-)-cleistenolide, (6S)-cleistenolide and 4-substituted cleistenolide analogues
    Benedekovic, Goran
    Farkas, Sandor
    Popsavin, Mirjana
    Stanisavljevic, Sladjana
    Djokic, Sanja
    Francuz, Jovana
    Kojic, Vesna
    Popsavin, Velimir
    BIOORGANIC & MEDICINAL CHEMISTRY, 2024, 111