Enantioselective Total Synthesis of the Selective PI3 Kinase Inhibitor Liphagal

被引:40
作者
Alvarez-Manzaneda, Enrique [1 ]
Chahboun, Rachid [1 ]
Alvarez, Esteban [1 ]
Cano, M. Jose [1 ]
Haidour, Ali [1 ]
Alvarez-Manzaneda, Ramon [2 ]
机构
[1] Univ Granada, Fac Ciencias, Dept Quim Organ, Inst Biotecnol, E-18071 Granada, Spain
[2] Univ Almeria, Fac Ciencias, Dept Quim Organ, Almeria 04120, Spain
关键词
ABSOLUTE-CONFIGURATION; CYCLIZATION;
D O I
10.1021/ol101173w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective total synthesis of liphagal, a selective inhibitor of PI3K alpha isolated from the marine sponge Aka coralliphaga, has been achieved. The novel tetracyclic "liphagane" skeleton is formed in one step, after the hydrogenation of a dihydroxydrimane phenol benzyl ether in the presence of cationic resin.
引用
收藏
页码:4450 / 4453
页数:4
相关论文
共 24 条
  • [1] Synthesis of terpenoid unsaturated 1,4-dialdehydes.: π-facial selectivity in the Diels-Alder reaction of the 1-vinyl-2-methylcyclohexene moiety of polycyclic systems with DMAD
    Abad, A
    Agulló, C
    Castelblanque, L
    Cuñat, AC
    Navarro, I
    de Arellano, MCR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13) : 4189 - 4192
  • [2] Alternative syntheses of versatile chiral intermediate for drimane sesquiterpenes and labdane diterpenes using (R,R)-cycloheptane-1,2-diol as a chiral auxiliary
    Akita, H
    Amano, Y
    Kato, K
    Kinoshita, M
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (04) : 725 - 732
  • [3] A thermal 6π electrocyclization strategy towards taiwaniaquinoids. First enantiospecific synthesis of (-)-taiwaniaquinone G
    Alvarez-Manzaneda, Enrique
    Chahboun, Rachid
    Cabrera, Eduardo
    Alvarez, Esteban
    Haidour, Ali
    Miguel Ramos, Jose
    Alvarez-Manzaneda, Ramon
    Hmamouchi, Mohammed
    Es-Samti, Hakima
    [J]. CHEMICAL COMMUNICATIONS, 2009, (05) : 592 - 594
  • [4] Natural product synthesis from (8aR)- and (8aS)-bicyclofarnesols: synthesis of (+)-wiedendiol A, (+)-norsesterterpene diene ester and (-)-subersic acid
    Arima, Yuusuke
    Kinoshita, Masako
    Akita, Hiroyuki
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (14) : 1701 - 1711
  • [5] BANERO AF, 1998, TETRADHEDRON, V54, P5635
  • [6] Marine natural products
    Blunt, John W.
    Copp, Brent R.
    Munro, Murray H. G.
    Northcote, Peter T.
    Prinsep, Michele R.
    [J]. NATURAL PRODUCT REPORTS, 2010, 27 (02) : 165 - 237
  • [7] DOMMGUE G, 1991, TETRAHEDRON LETT, V32, P1765
  • [8] Enantiospecific, Biosynthetically Inspired Formal Total Synthesis of (+)-Liphagal
    George, Jonathan H.
    Baldwin, Jack E.
    Adlington, Robert M.
    [J]. ORGANIC LETTERS, 2010, 12 (10) : 2394 - 2397
  • [9] Bioactive metabolites from the Caribbean sponge Aka coralliphagum
    Grube, Achim
    Assmann, Michael
    Lichte, Ellen
    Sasse, Florenz
    Pawlik, Joseph R.
    Koeck, Matthias
    [J]. JOURNAL OF NATURAL PRODUCTS, 2007, 70 (04): : 504 - 509
  • [10] The first total synthesis and determination of the absolute configuration of chapecoderin A, B and C
    Hagiwara, H
    Takeuchi, F
    Nozawa, M
    Hoshi, T
    Suzuki, T
    [J]. TETRAHEDRON, 2004, 60 (09) : 1983 - 1989