A Concise Asymmetric Total Synthesis of (+)-Brevisamide

被引：43
作者：
Herrmann, Aaron T. [1 ]
Martinez, Steven R. [1 ]
Zakarian, Armen [1 ]
机构：
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 14期
基金：
美国国家卫生研究院;
关键词：
DINOFLAGELLATE KARENIA-BREVIS; ABSOLUTE-CONFIGURATION; VINYLSILANES; CONFIRMATION; POLYETHERS; ACETYLENES;
D O I：
10.1021/ol201283n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new protecting-group-free synthesis of the marine monocyclic ether (+)-brevisamide is reported. The enantioselective synthesis utilizes a key asymmetric Henry reaction and an Achmatowicz rearrangement for the formation of the tetrahydropyran ring. A penultimate Stille cross-coupling allows for an efficient installation of the conjugated (E,E)-diene side chain ultimately delivering (+)-brevisamide.
引用
收藏
页码：3636 / 3639
页数：4
相关论文
共 43 条
  • [1] SYNTHESIS OF METHYL 2,3-DIDEOXY-DL-ALK-2-ENOPYRANOSIDES FROM FURAN COMPOUNDS - GENERAL APPROACH TO TOTAL SYNTHESIS OF MONOSACCHARIDES
    ACHMATOWICZ, O
    BUKOWSKI, P
    SZECHNER, B
    ZWIERZCHOWSKA, Z
    ZAMOJSKI, A
    [J]. TETRAHEDRON, 1971, 27 (10) : 1973 - +
  • [2] Stereocontrol in organic synthesis using silicon-containing compounds. Studies directed towards the synthesis of ebelactone A
    Archibald, SC
    Barden, DJ
    Bazin, JFY
    Fleming, I
    Foster, CF
    Mandal, AK
    Mandal, AK
    Parker, D
    Takaki, K
    Ware, AC
    Williams, ARB
    Zwicky, AB
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (07) : 1051 - 1064
  • [3] A synthesis strategy yielding skeletally diverse small molecules combinatorially
    Burke, MD
    Berger, EM
    Schreiber, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (43) : 14095 - 14104
  • [4] A Strategy for the Late-Stage Divergent Syntheses of Scyphostatin Analogues
    Cha, Jacob Y.
    Burnett, G. Leslie
    Huang, Yaodong
    Davidson, Jarrod B.
    Pettus, Thomas R. R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05) : 1361 - 1371
  • [5] Total synthesis of lucilactaene, a cell cycle inhibitor active in p53-inactive cells
    Coleman, RS
    Walczak, MC
    Campbell, EL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) : 16038 - 16039
  • [6] Corey E.J., 1972, TETRAHEDRON, V36, P3769
  • [7] Total Synthesis of Brevisamide
    Fadeyi, Olugbeminiyi O.
    Lindsley, Craig W.
    [J]. ORGANIC LETTERS, 2009, 11 (17) : 3950 - 3952
  • [8] REACTION OF A SILYL-COPPER REAGENT WITH ACETYLENES - A NEW SYNTHESIS OF VINYLSILANES
    FLEMING, I
    ROESSLER, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (06) : 276 - 277
  • [9] OBSERVATIONS ON VARIOUS SILYL-CUPRATE REAGENTS
    FLEMING, I
    NEWTON, TW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08): : 1805 - 1808
  • [10] THE SILYLCUPRATION OF ACETYLENES - A SYNTHESIS OF VINYLSILANES
    FLEMING, I
    NEWTON, TW
    ROESSLER, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09): : 2527 - 2532
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