ASYMMETRIC-SYNTHESIS FROM PYRIDINES - USE OF NEW CHIRAL 1,4-DIHYDROPYRIDINES IN A SHORT SYNTHESIS OF 5,8-DISUBSTITUTED INDOLIZIDINE (+)-209B

被引:51
|
作者
GNECCO, D [1 ]
MARAZANO, C [1 ]
DAS, BC [1 ]
机构
[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1039/c39910000625
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthetic potentiality of chiral oxazolidines, prepared from 3-picoline via a 1,4-dihydropyridine intermediate, has been illustrated by an expeditious route to the 5,8-disubstituted indolizidine alkaloid (+)-209B.
引用
收藏
页码:625 / 626
页数:2
相关论文
共 50 条
  • [21] Reactivity of bis-vinylphosphates obtained from imide derivatives. Synthesis of 2,6-disubstituted 1,4-dihydropyridines
    Mousset, D
    Gillaizeau, I
    Hassan, J
    Lepifre, F
    Bouyssou, P
    Coudert, G
    TETRAHEDRON LETTERS, 2005, 46 (21) : 3703 - 3705
  • [22] EFFICIENT SYNTHESIS OF 5,8-DISUBSTITUTED 1,4-DIHYDROBENZOXATHIIN-3-OXIDES AND THEIR ISOMERIC STRUCTURES, 4,7-DISUBSTITUTED-1,3-DIHYDROBENZO[B]THIOPHENE-2,2-DIOXIDES
    ATTARDO, G
    WANG, WY
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 364 - ORGN
  • [23] Application of novel nanomagnetic metal–organic frameworks as a catalyst for the synthesis of new pyridines and 1,4-dihydropyridines via a cooperative vinylogous anomeric based oxidation
    Hassan Sepehrmansourie
    Mahmoud Zarei
    Mohammad Ali Zolfigol
    Saeed Babaee
    Sadegh Rostamnia
    Scientific Reports, 11
  • [24] Cascadic heterocyclization in synthesis of new 1,4-dihydropyridines and 1,4,5,6,7,8-hexahydroquinolines containing sulfur
    Litvinov, V.P.
    Krivolysko, S.G.
    Rusanov, E.B.
    2001, National Academy of Sciences (377)
  • [25] Flexible synthetic routes to poison-frog alkaloids of the 5,8-disubstituted indolizidine-class I: synthesis of common lactam chiral building blocks and application to the synthesis of (-)-203A, (-)-205A, and (-)-219F
    Toyooka, Naoki
    Zhou, Dejun
    Nemoto, Hideo
    Garraffo, H. Martin
    Spande, Thomas F.
    Daly, John W.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2007, 3
  • [26] Synthesis of 5-Substituted 7,8-Benzomorphans by Intramolecular Cyclization of N-Protected 4,4-Disubstituted 1,4-Dihydropyridines
    Schmaunz, Cornelia E.
    Pabel, Joerg
    Wanner, Klaus T.
    SYNTHESIS-STUTTGART, 2010, (13): : 2147 - 2160
  • [27] Application of novel nanomagnetic metal-organic frameworks as a catalyst for the synthesis of new pyridines and 1,4-dihydropyridines via a cooperative vinylogous anomeric based oxidation
    Sepehrmansourie, Hassan
    Zarei, Mahmoud
    Zolfigol, Mohammad Ali
    Babaee, Saeed
    Rostamnia, Sadegh
    SCIENTIFIC REPORTS, 2021, 11 (01)
  • [28] Cascade heterocyclization in the synthesis of new sulfur-containing 1,4-dihydropyridines and 1,4,5,6,7,8-hexahydroquinolines
    Litvinov, VP
    Krivokolysko, SG
    Rusanov, EB
    DOKLADY CHEMISTRY, 2001, 377 (4-6) : 94 - 100
  • [29] Bronsted Acid-Thiourea Co-catalysis: Asymmetric Synthesis of Functionalized 1,4-Dihydropyridines from β-Enamino Esters and α,β-Unsaturated Aldehydes
    Yoshida, Kohzo
    Inokuma, Tsubasa
    Takasu, Kiyosei
    Takemoto, Yoshiji
    SYNLETT, 2010, (12) : 1865 - 1869
  • [30] A SHORT SYNTHESIS OF INDOLIZIDINE (+)-209B FROM (3R,6S,8aS)-(-)-6-METHYL-3-PHENYLHEXAHYDROOXAZOLO[3,2-a]PYRIDIN-5-ONE
    Gnecco, Dino
    Lumbreras, Ana M.
    Teran, Joel L.
    Galindo, Alberto
    Juarez, Jorge R.
    Orea, Maria L.
    Castro, Alejandro
    Enriquez, Raul G.
    Reynolds, William F.
    HETEROCYCLES, 2009, 78 (10) : 2589 - 2594