A new asymmetric 1,4-addition method: application to the synthesis of the HIV non-nucleoside reverse transcriptase inhibitor DPC 961

被引:47
作者
Magnus, NA [1 ]
Confalone, PN [1 ]
Storace, L [1 ]
机构
[1] DuPont Pharmaceut Co, Chem Proc R&D, Chambers Works, Deepwater, NJ 08023 USA
关键词
D O I
10.1016/S0040-4039(00)00331-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric synthesis of the HIV non-nucleoside reverse transcriptase inhibitor (NNRTI) DPC 961 is achieved in three steps with an overall yield of >55%. The asymmetry is induced by the chiral auxiliary (R)-(+)-alpha-methylbenzylamine, utilizing a new asymmetric 1,4-addition protocol. (C) 2000 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3015 / 3019
页数:5
相关论文
共 13 条
  • [1] BRITCHER SF, 1993, Patent No. 04047
  • [2] Expanded-spectrum nonnucleoside reverse transcriptase inhibitors inhibit clinically relevant mutant variants of human immunodeficiency virus type 1
    Corbett, JW
    Ko, SS
    Rodgers, JD
    Jeffrey, S
    Bacheler, LT
    Klabe, RM
    Diamond, S
    Lai, CM
    Rabel, SR
    Saye, JA
    Adams, SP
    Trainor, GL
    Anderson, PS
    Erickson-Viitanen, SK
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1999, 43 (12) : 2893 - 2897
  • [3] GHEORGHUI CV, 1943, CHEM BER, V76, P994
  • [4] LITHIUM ALKOXIDES OF CINCHONA ALKALOIDS AS CHIRAL CONTROLLERS FOR ENANTIOSELECTIVE ACETYLIDE ADDITION TO CYCLIC N-ACYL KETIMINES
    HUFFMAN, MA
    YASUDA, N
    DECAMP, AE
    GRABOWSKI, EJJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) : 1590 - 1594
  • [5] QUINAZOLINES AND 1,4-BENZODIAZEPINES .28. SUBSTITUTED 2(3H)-QUINAZOLINONES AND -QUINAZOLINETHIONES
    METLESICS, W
    SILVERMAN, G
    TOOME, V
    STERNBACH, LH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (04) : 1007 - +
  • [6] Synthesis and evaluation of benzoxazinones as HIV-1 reverse transcriptase inhibitors.: Analogs of Efavirenz (SUSTIVA™)
    Patel, M
    McHugh, RJ
    Cordova, BC
    Klabe, RM
    Erickson-Viitanen, S
    Trainor, GL
    Ko, SS
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (22) : 3221 - 3224
  • [7] Synthesis and evaluation of analogs of Efavirenz (SUSTIVA™) as HIV-1 reverse transcriptase inhibitors
    Patel, M
    Ko, SS
    McHugh, RJ
    Markwalder, JA
    Srivastava, AS
    Cordova, BC
    Klabe, RM
    Erickson-Viitanen, S
    Trainor, GL
    Seitz, SP
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (19) : 2805 - 2810
  • [8] Practical asymmetric synthesis of efavirenz (DMP 266), an HIV-1 reverse transcriptase inhibitor
    Pierce, ME
    Parsons, RL
    Radesca, LA
    Lo, YS
    Silverman, S
    Moore, JR
    Islam, Q
    Choudhury, A
    Fortunak, JMD
    Nguyen, D
    Luo, C
    Morgan, SJ
    Davis, WP
    Confalone, PN
    Chen, CY
    Tillyer, RD
    Frey, L
    Tan, LS
    Xu, F
    Zhao, DL
    Thompson, AS
    Corley, EG
    Grabowski, EJJ
    Reamer, R
    Reider, PJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) : 8536 - 8543
  • [9] REISSERT A, 1926, CHEM BER, V39, P2494
  • [10] Tan L, 1999, ANGEW CHEM INT EDIT, V38, P711, DOI 10.1002/(SICI)1521-3773(19990301)38:5<711::AID-ANIE711>3.0.CO