Synthetic approaches to rapamycin .3. Synthesis of a C1-C21 fragment

被引:0
作者
Harris, L
Jarowicki, K
Kocienski, P
机构
[1] UNIV SOUTHAMPTON,DEPT CHEM,SOUTHAMPTON SO17 1BJ,HANTS,ENGLAND
[2] GLAXO WELLCOME RES CTR,STEVENAGE SG1 2NY,HERTS,ENGLAND
关键词
rapamycin; asymmetric allylation; asymmetric hydrogenation; Heck reaction; immunosuppressant; ketenedithioacetal; alpha-oxoketene;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Key steps in two alternative approaches to the C10-C21 fragments 4 and 17 of the immunosuppressant rapamycin employ catalytic asymmetric allylation and catalytic asymmetric hydrogenation to introduce the first stereogenic centre at C14. Appendage of C1-C9 via trapping of an a-oxoketene intermediate generates the C1-C21 fragment 5.
引用
收藏
页码:903 / &
页数:4
相关论文
共 50 条
  • [31] Total Synthesis of (±)-Cephanolides B and C via a Palladium-Catalyzed Cascade Cyclization and Late-Stage sp3 C-H Bond Oxidation
    Xu, Lun
    Wang, Chao
    Gao, Ziwei
    Zhao, Yu-Ming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (16) : 5653 - 5658
  • [32] Synthesis of 3-C-Branched Kdo Analogues via Sonogashira Coupling of 3-lodo Kdo Glycal with Terminal Alkynes
    Fan, Wenjing
    Chen, Yan
    Lou, Qixin
    Zhuang, Liqin
    Yang, You
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (11) : 6171 - 6177
  • [33] Hydrogenolysis of the C-O bond of hydroxylactams as a convenient method for the synthesis of substituted isoindolin-1-ones
    Sagirova, Zh R.
    Starodubtseva, E. V.
    Turova, O. V.
    Vinogradov, M. G.
    RUSSIAN CHEMICAL BULLETIN, 2013, 62 (04) : 1032 - 1037
  • [34] Synthesis of Five-Membered Cyclic Phosphinic Acids via the [4C+1P] Cyclization of 1,3-Dienes with a Combination of PBr3 and P(OMe)3 as the P(III) Source
    Li, Ang
    Han, Fu-She
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (17) : 12224 - 12235
  • [35] The synthesis of (η3-C3H5)Pd{Si[N(tBu)CH]2}Cl and the catalytic property for Heck reaction
    Zhang, Ming
    Liu, Xiaoli
    Shi, Chaojun
    Ren, Chunxia
    Ding, Yuqiang
    Roesky, Herbert W.
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2008, 634 (10): : 1755 - 1758
  • [36] Tetrabutylammonium-Bromide-Promoted Synthesis of Spirooxindoles through Alkyne-Aldehyde C-C Coupling and 1,3-Dipolar Cycloaddition Using Ytterbium Triflate Catalyst
    Teja, Chitrala
    Khan, Fazlur Rahman Nawaz
    CHEMISTRYSELECT, 2020, 5 (21): : 6470 - 6474
  • [37] A New Synthesis of 5-Arylbenzo[c] xanthones from Photoinduced Electrocyclisation and Oxidation of (E)-3-Styrylflavones
    Rocha, Djenisa H. A.
    Pinto, Diana C. G. A.
    Silva, Artur M. S.
    Patonay, Tamas
    Cavaleiroa, Jose A. S.
    SYNLETT, 2012, (04) : 559 - 564
  • [38] Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation of diverse C(sp3)-H bonds
    Wen, Xin
    Wang, Yong
    Zhang, X. Peter
    CHEMICAL SCIENCE, 2018, 9 (22) : 5082 - 5086
  • [39] Tristetraprolin regulates Cyclin D1 and c-myc mRNA stability in response to rapamycin in an Akt-dependent manner via p38 MAPK signaling
    Marderosian, M.
    Sharma, A. P.
    Funk, A. P.
    Vartanian, R.
    Masri, J.
    Jo, O. D.
    Gera, J. F.
    ONCOGENE, 2006, 25 (47) : 6277 - 6290
  • [40] Tristetraprolin regulates Cyclin D1 and c-Myc mRNA stability in response to rapamycin in an Akt-dependent manner via p38 MAPK signaling
    M Marderosian
    A Sharma
    A P Funk
    R Vartanian
    J Masri
    O D Jo
    J F Gera
    Oncogene, 2006, 25 : 6277 - 6290