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
  • [41] Synthetic studies on spongistatins: synthesis of the C29-C44 fragment
    Samadi, M
    Munoz-Letelier, C
    Poigny, S
    Guyot, M
    TETRAHEDRON LETTERS, 2000, 41 (18) : 3349 - 3353
  • [42] SYNTHETIC STUDY OF SALINOMYCIN (SYNTHESIS OF C-18-C-29 FRAGMENT)
    HORITA, K
    NAGATO, S
    OIKAWA, Y
    YONEMITSU, O
    HETEROCYCLES, 1986, 24 (01) : 277 - 277
  • [43] Synthesis of the C9-C21 fragment of debromoaplysiatoxin and oscillatoxins A and D
    Cosp, Annabel
    Llacer, Enric
    Romea, Pedro
    Urpi, Felix
    TETRAHEDRON LETTERS, 2006, 47 (32) : 5819 - 5823
  • [44] New synthetic route to the C.14-C.21 fragment of halichondrin B.
    Yu, MJ
    Tremblay, L
    Davis, HA
    Palme, MH
    Sexton, KA
    Zheng, W
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U221 - U221
  • [45] Enantioselective Synthesis of the C(1)-C(11) Fragment of Tedanolide C
    Geist, Julie G.
    Barth, Roland
    Roush, William R.
    ORGANIC LETTERS, 2013, 15 (01) : 58 - 61
  • [46] Synthesis of the C1-C12 Fragment of Calyculin C
    Konstantinova, Olga V.
    Koskinen, Ari M. P.
    SYNTHESIS-STUTTGART, 2019, 51 (01): : 285 - 295
  • [47] Synthetic studies of HIV-active Didemnaketal A analogue - Synthesis of a C1-C7 fragment
    Jia, YX
    Wang, PZ
    Wu, B
    Tu, YQ
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2000, 21 (05): : 729 - 730
  • [48] Synthetic studies toward amphidinolide B1:: Synthesis of the C9-C26 fragment
    Zhang, W
    Carter, RG
    ORGANIC LETTERS, 2005, 7 (19) : 4209 - 4212
  • [49] SYNTHETIC STUDIES ON MACROLIDES .1. STEREOSPECIFIC SYNTHESIS OF 9-C-11-C FRAGMENT OF METHYNOLIDE
    SHIYONOK, AI
    SVIRIDOV, AF
    CHIZHOV, OS
    BIOORGANICHESKAYA KHIMIYA, 1977, 3 (07): : 914 - 919
  • [50] RAPAMYCIN SYNTHETIC STUDIES .1. CONSTRUCTION OF THE C(27)-C(42) SUBUNIT
    SMITH, AB
    CONDON, SM
    MCCAULEY, JA
    LEAHY, JW
    LEAZER, JL
    MALECZKA, RE
    TETRAHEDRON LETTERS, 1994, 35 (28) : 4907 - 4910