Synthesis of the C1-C20 and C15-C27 Segments of Aplyronine A

被引:18
|
作者
Hong, Wan Pyo [1 ]
Noshi, Mohammad N. [1 ]
El-Awa, Ahmad [1 ]
Fuchs, Philip L. [1 ]
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
关键词
POTENT ANTITUMOR SUBSTANCE; MARINE MACROLIDE SYNTHESIS; ORGANIC-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ALDEHYDES; CONVERSION; SULFONES; ORIGIN; STEREOTETRADS;
D O I
10.1021/ol2024746
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of C1-C20 and C15-C27 segments of Aplyronine A is described. Oxidative cleavage of cyclic vinyl sulfones has been used to prepare key fragments of Aplyronine A. Key precursors are united by Horner-Wadsworth-Emmons and Julia-Kociensky olefination for the respective elaboration of the C1-C20 and C15-C27 segments.
引用
收藏
页码:6342 / 6345
页数:4
相关论文
共 50 条
  • [21] A synthesis of the C(17)-C(27) fragment of bryostatin 1
    Green, Anthony P.
    Hardy, Simon
    Thomas, Eric J.
    SYNLETT, 2008, (14) : 2103 - 2106
  • [22] Absolute stereochemistry of amphidinolide C: synthesis of C-1-C-10 and C-17-C-29 segments
    Kubota, T
    Tsuda, M
    Kobayashi, J
    TETRAHEDRON, 2003, 59 (10) : 1613 - 1625
  • [23] GAS CHROMATOGRAPHY MASS SPECTROMETRY OF C1-C20 FATTY-ACID BENZYL-ESTERS
    HINTZE, U
    ROPER, H
    GERCKEN, G
    JOURNAL OF CHROMATOGRAPHY, 1973, 87 (02): : 481 - 489
  • [24] Enantioselective synthesis of the C1-C15 fragment of dolabelide C
    Vincent, Aurelie
    Prunet, Joeelle
    SYNLETT, 2006, (14) : 2269 - 2271
  • [25] ENANTIOSPECIFIC SYNTHESIS OF THE C-17-C-20 AND C-21-C-27 SYNTHONS OF THE ANTINEOPLASTIC MACROLIDE BRYOSTATINS
    ROY, R
    REY, AW
    CHARRON, M
    MOLINO, R
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (18) : 1308 - 1310
  • [26] SYNTHESIS OF THE C1-C7 AND C8-C18 SEGMENTS OF ent-AMPHIDININ A
    Ishiyama, Haruaki
    Hangyou, Masahiro
    Nakatsu, Ayumi
    Mori, Yuta
    Kobayashi, Jun'ichi
    HETEROCYCLES, 2015, 90 (02) : 1254 - 1273
  • [27] A synthesis of the C1-C15 domain of the halichondrins
    Jackson, Katrina L.
    Henderson, James A.
    Morris, Jonathan C.
    Motoyoshi, Hajime
    Phillips, Andrew J.
    TETRAHEDRON LETTERS, 2008, 49 (18) : 2939 - 2941
  • [28] Halichondrin B: Synthesis of the C(1)-C(15) subunit
    Burke, SD
    Jung, KW
    Lambert, WT
    Phillips, JR
    Klovning, JJ
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13): : 4070 - 4087
  • [29] Synthesis of the C1-C15 domain of the thyrsiferols
    Gonzalez, IC
    Forsyth, CJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U185 - U185
  • [30] The synthesis of C-1 to C-15 of discodermolide
    Harried, SS
    Strawn, MA
    Myles, DC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 80 - ORGN