A sultone approach to the C(1)-C(18) moiety of pamamycin-607

被引：31
作者：
Bernsmann, H
Fröhlich, R
Metz, P
机构：
[1] Tech Univ Dresden, Inst Organ Chem, D-01062 Dresden, Germany
[2] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 22期
关键词：
antibiotics; Diels-Alder reactions; sultones; hydroboration;
D O I：
10.1016/S0040-4039(00)00659-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly advanced enantiomerically pure C(1)-C(18) precursor of the larger fragment of the macro-diolide pamamycin-607 has been synthesized. The stereotriad C(7)-C(9) between the two heterocyclic rings of the target was generated using a diastereoselective hydroboration controlled by minimization of allylic 1,3-strain. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4347 / 4351
页数：5
相关论文
共 30 条
  • [1] Arista L, 1997, SYNLETT, P627
  • [2] CONVENIENT GENERAL-METHOD FOR THE PREPARATION OF PRIMARY ALKYLLITHIUMS BY LITHIUM IODINE EXCHANGE
    BAILEY, WF
    PUNZALAN, ER
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) : 5404 - 5406
  • [3] Toward the synthesis of pamamycin-607
    Bernsmann, H
    Hungerhoff, B
    Fechner, R
    Fröhlich, R
    Metz, P
    [J]. TETRAHEDRON LETTERS, 2000, 41 (11) : 1721 - 1724
  • [4] GRAFE U, 1994, PHARMAZIE, V49, P343
  • [5] Protonophoric activities of helioferin and pamamycin, lipophilic tertiary amine antibiotics from Mycogone rosea and Streptomyces aurantiacus
    Grigoriev, P
    Berg, A
    Schlegel, R
    Grafe, U
    [J]. BIOELECTROCHEMISTRY AND BIOENERGETICS, 1996, 39 (02): : 295 - 298
  • [6] Härtl A, 1998, J ANTIBIOT, V51, P1040
  • [7] ALLYLIC 1,3-STRAIN AS A CONTROLLING FACTOR IN STEREOSELECTIVE TRANSFORMATIONS
    HOFFMANN, RW
    [J]. CHEMICAL REVIEWS, 1989, 89 (08) : 1841 - 1860
  • [8] KELLER E, 1997, SCHAKAL 97 COMPUTER
  • [9] ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITY OF PAMAMYCIN-607, AN AERIAL MYCELIUM-INDUCING SUBSTANCE FROM STREPTOMYCES-ALBONIGER
    KONDO, S
    YASUI, K
    NATSUME, M
    KATAYAMA, M
    MARUMO, S
    [J]. JOURNAL OF ANTIBIOTICS, 1988, 41 (09) : 1196 - 1204
  • [10] STRUCTURE OF PAMAMYCIN-607, AN AERIAL MYCELIUM-INDUCING SUBSTANCE OF STREPTOMYCES-ALBONIGER
    KONDO, S
    YASUI, K
    KATAYAMA, M
    MARUMO, S
    KONDO, T
    HATTORI, H
    [J]. TETRAHEDRON LETTERS, 1987, 28 (47) : 5861 - 5864
123