SYNTHESIS OF THE C1-C7 AND C8-C18 SEGMENTS OF ent-AMPHIDININ A

被引:2
|
作者
Ishiyama, Haruaki [1 ]
Hangyou, Masahiro [1 ]
Nakatsu, Ayumi [1 ]
Mori, Yuta [1 ]
Kobayashi, Jun'ichi [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
关键词
Amphidinin A; Ampheiniam sp; Dinoflagellate; CATALYTIC ASYMMETRIC EPOXIDATION; SPIN-COUPLING-CONSTANTS; STEREOSELECTIVE-SYNTHESIS; CONFIGURATION; ALDEHYDES; SULFONES; ALCOHOLS; FRAGMENT;
D O I
10.3987/COM-14-S(K)107
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereoselective synthesis of the C1-C7 and C8-C18 segments of the enantiomer of amphidinin A, a cytotoxic polyketide from the culture cells of a symbiotic marine dinoflagellate Amphidinium sp. (strain Y-5), has been achieved, utilizing sulfone-aldehyde coupling, Sharpless asymmetric dihydroxylation, Katsuki-Sharpless asymmetric epoxidation, and Julia-Kocienski olefination.
引用
收藏
页码:1254 / 1273
页数:20
相关论文
共 50 条
  • [21] Oxidation and combustion mechanisms of paraffin hydrocarbons: Transfer from C1-C7 to C8H18, C9H20, and C10H22
    V. Ya. Basevich
    A. A. Belyaev
    S. N. Medvedev
    V. S. Posvyanskii
    S. M. Frolov
    Russian Journal of Physical Chemistry B, 2011, 5 : 974 - 990
  • [22] Stereoselective synthesis towards the C8-C18 subunit of pamamycin-607 induced by a chiral sulfoxide group
    Solladié, G
    Salom-Roig, XJ
    Hanquet, G
    TETRAHEDRON LETTERS, 2000, 41 (04) : 551 - 554
  • [23] Towards the total synthesis of pamamycin-607:: Preparation of the eastern part-(C8-C18 fragment)
    Mandville, G
    Bloch, R
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (09) : 2303 - 2307
  • [24] 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
  • [25] Influence of carbon number of C1-C7 hydrocarbons on PAH formation
    Dandajeh, Hamisu Adamu
    Ladommatos, Nicos
    Hellier, Paul
    Eveleigh, Aaron
    FUEL, 2018, 228 : 140 - 151
  • [26] Synthesis of southern (C1′-C11′) and eastern (C8-C18) fragments of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger
    Kiyota, H
    Furuya, Y
    Kuwahara, S
    Oritani, T
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2001, 65 (12) : 2630 - 2637
  • [27] Preparation of the three C1-C7, C8-C15, and C16-N22 fragments of the Hsp90 inhibitor herbimycin A
    Centonze-Audureau, S
    Porée, FH
    Betzer, JF
    Brion, JD
    Pancrazi, A
    Ardisson, J
    SYNLETT, 2005, (06) : 981 - 985
  • [28] VISUAL PIGMENT DISPERSED IN C8-C18 FATTY-ACID SUGAR ESTER SOLUTIONS
    MOTOYAMA, H
    BOUCHER, F
    KAWASE, N
    KITO, Y
    VISION RESEARCH, 1984, 24 (11) : 1691 - 1691
  • [29] Synthetic studies of the 18-membered antitumor macrolide, tedanolide.: 3.: Stereocontrolled synthesis of the C1-C12 part via a synthesis of the C1-C7 fragment by a mismatched but efficient sharpless dihydroxylation and its coupling with the C8-C11 fragment
    Matsushima, T
    Mori, M
    Zheng, BZ
    Maeda, H
    Nakajima, N
    Uenishi, J
    Yonemitsu, O
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1999, 47 (03) : 308 - 321
  • [30] Evaporation rates and vapor pressures of the even-nunibered C8-C18 monocarboxylic acids
    Cappa, Christopher D.
    Lovejoy, Edward R.
    Ravishankara, A. R.
    JOURNAL OF PHYSICAL CHEMISTRY A, 2008, 112 (17): : 3959 - 3964