Synthesis of C16-C27-fragments of bryostatins modified by 20,20-difluorination

被引：7
|
作者：
Mears, Paul R. [1 ]
Thomas, Eric J. [1 ]
机构：
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 26期
基金：
英国工程与自然科学研究理事会;
关键词：
Bryostatins; Difluorination; PKC activation; Total synthesis; Anticancer activity; KINASE-C AFFINITY; BIOLOGICAL-ACTIVITIES; ASYMMETRIC-SYNTHESIS; B-RING; ANALOGS; INHIBITORS; DESIGN; ESTER; CONSTRUCTION; DERIVATIVES;
D O I：
10.1016/j.tetlet.2015.05.007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Hydroxytetrahydropyrans corresponding to the C16-C27 fragment of bryostatins which have been difluorinated at C20 (bryostatin numbering) have been synthesised. The fluorine substituents were introduced by difluoroallylation. An (E)-selective Wittig reaction using a stabilised ylide provided the required methoxycarbonylmethylene substituent with excellent stereoselectivity. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3975 / 3979
页数：5
相关论文
共 50 条
  • [1] Towards 20,20-difluorinated bryostatin: synthesis and biological evaluation of C17,C27-fragments
    Mears P.R.
    Hoekman S.
    Rye C.E.
    Bailey F.P.
    Byrne D.P.
    Eyers P.A.
    Thomas E.J.
    Organic and Biomolecular Chemistry, 2019, 17 (06): : 1487 - 1505
  • [2] Towards 20,20-difluorinated bryostatin: synthesis and biological evaluation of C17,C27-fragments
    Mears, Paul R.
    Hoekman, Steven
    Rye, Claire E.
    Bailey, Fiona P.
    Byrne, Dominic P.
    Eyers, Patrick A.
    Thomas, Eric J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (06) : 1487 - 1505
  • [3] Synthetic approaches to the C11-C27 fragments of bryostatins
    Green, Anthony P.
    Hardy, Simon
    Thomas, Eric J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (44) : 9475 - 9496
  • [4] BRYOSTATINS - THE ASYMMETRIC-SYNTHESIS OF THE C-1-C-9 AND C-17-C-27 FRAGMENTS
    DEBRABANDER, J
    VANDEWALLE, M
    SYNTHESIS-STUTTGART, 1994, (08): : 855 - 865
  • [5] Synthesis of the C(1)-C(16) fragment of bryostatins
    O'Brien, M
    Taylor, NH
    Thomas, EJ
    TETRAHEDRON LETTERS, 2002, 43 (31) : 5491 - 5494
  • [6] SYNTHETIC STUDIES ON BRYOSTATINS, POTENT ANTINEOPLASTIC AGENTS - SYNTHESIS OF THE C-17-C-27 FRAGMENT OF C-20 OXYGENATED BRYOSTATINS
    OHMORI, K
    NISHIYAMA, S
    YAMAMURA, S
    TETRAHEDRON LETTERS, 1995, 36 (36) : 6519 - 6522
  • [7] BRYOSTATINS - THE ASYMMETRIC-SYNTHESIS OF C1-C9 AND C11-C16 FRAGMENTS
    DEBRABANDER, J
    VANHESSCHE, K
    VANDEWALLE, M
    TETRAHEDRON LETTERS, 1991, 32 (24) : 2821 - 2824
  • [8] An approach to the synthesis of the C(17)-C(27) fragment of bryostatins
    Baxter, J
    Mata, EG
    Thomas, EJ
    TETRAHEDRON, 1998, 54 (47) : 14359 - 14376
  • [9] Asymmetric synthesis of the C(10)-C(16) segment of the bryostatins
    Lampe, TFJ
    Hoffmann, HMR
    TETRAHEDRON LETTERS, 1996, 37 (43) : 7695 - 7698
  • [10] A stereoselective synthesis of the C(1)-C(16) fragment of the bryostatins
    Ball, M
    Baron, A
    Bradshaw, B
    Omori, H
    MacCormick, S
    Thomas, EJ
    TETRAHEDRON LETTERS, 2004, 45 (47) : 8737 - 8740
12345