A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids

[1]  國郎 小笠原,et al.  Chem. Pharm. Bull.(オピニオン) , 2007 .

[2]  F. A. Davis,et al.  Asymmetric Synthesis of Ring Functionalized trans-2,6- Disubstituted Piperidines from N-Sulfinyl δ-Amino β-Keto Phosphonates. Total Synthesis of (−)-Myrtine , 2007 .

[3]  W. Hua,et al.  A concise and enantioselective approach to the total synthesis of (-)-lasubine I , 2006 .

[4]  T. Rovis,et al.  Enantioselective rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes: application to the total synthesis of (+)-lasubine II. , 2006, Journal of the American Chemical Society.

[5]  Katsunori Tanaka,et al.  Synthesis of 2,4,6-trisubstituted chiral piperidines and (-)-dendroprimine by one-pot asymmetric azaelectrocyclization protocol. , 2006, Organic letters.

[6]  R. Remuson,et al.  Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion , 2006 .

[7]  Amos B. Smith,et al.  A general, convergent strategy for the construction of indolizidine alkaloids: total syntheses of (-)-indolizidine 223AB and alkaloid (-)-205B. , 2006, The Journal of organic chemistry.

[8]  N. Toyooka,et al.  Synthesis of (-)-5-Epiindolizidine 167B and Formal Synthesis of 5E,9Z-Indolizidine 223AB , 2005 .

[9]  S. Martin,et al.  Cascade iminium ion reactions for the facile synthesis of quinolizidines. Concise syntheses of (+/-)-epilupinine and (-)-epimyrtine. , 2005, Organic letters.

[10]  Michael D. Hamilton,et al.  Synthesis of the quinolizidine alkaloids (-)-lasubine II and (+/-)-myrtine by conjugate addition and intramolecular acylation of amino esters with acetylenic sulfones. , 2005, The Journal of organic chemistry.

[11]  Tetrahedron: Asymmetry , 2005 .

[12]  A. Katritzky,et al.  Heterocycles , 2022, Pharmaceutical Chemistry Journal.

[13]  D. Gnecco,et al.  Controlled reduction of 5-alkyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium iodide: enantioselective synthesis of (−)-dihydropinidine and (+)-indolizidine 167B , 2004 .

[14]  S. Blechert,et al.  Concise enantioselective synthesis of (-)-lasubine II , 2004 .

[15]  J. Gramain,et al.  Enantioselective synthesis of (-)-dendroprimine and isomers. , 2004, Journal of natural products.

[16]  S. Baskaran,et al.  Epoxide-initiated cationic cyclization of azides: a novel method for the stereoselective construction of 5-hydroxymethyl azabicyclic compounds and application in the stereo- and enantioselective total synthesis of (+)- and (-)-indolizidine 167B and 209D. , 2004, The Journal of organic chemistry.

[17]  Amos B. Smith,et al.  Multicomponent linchpin coupling of silyl dithianes employing an N-Ts aziridine as the second electrophile: synthesis of (-)-indolizidine 223AB. , 2004, Organic letters.

[18]  J. Aubé,et al.  Ring expansive routes to quinolizidine alkaloids: formal synthesis of (-)-lasubine II. , 2003, Organic letters.

[19]  F. A. Davis,et al.  Asymmetric Synthesis of the Quinolizidine Alkaloid (−)-Epimyrtine with Intramolecular Mannich Cyclization and N-Sulfinyl δ-Amino β-Ketoesters , 2003 .

[20]  C. Escolano,et al.  Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived delta-lactam. , 2003, The Journal of organic chemistry.

[21]  B. Varghese,et al.  Epoxide-initiated electrophilic cyclization of azides: a novel route for the stereoselective construction of azabicyclic ring systems and total synthesis of (+/-)-indolizidine 167B and 209D. , 2003, Organic letters.

[22]  Y. Troin,et al.  Stereoselective synthesis of C-6 substituted pipecolic acid derivatives. Formal synthesis of (+)-indolizidine 167B and (+)-indolizidine 209D , 2002 .

[23]  S. Blechert,et al.  A new and efficient synthesis of (−)-indolizidine 167B by tandem metathesis , 2002 .

[24]  Michael D. Hamilton,et al.  Total Synthesis of (-)-lasubine II by the conjugate addition and intramolecular acylation of an amino ester with an acetylenic sulfone. , 2002, Organic letters.

[25]  Manuela M. Pereira,et al.  A radical approach towards indolizidine 167B , 2002 .

[26]  D. Ma,et al.  Two-component method to enantiopure quinolizidinones and Indolizidinones. Total synthesis of (-)-lasubine II. , 2001, Organic letters.

[27]  G. Sulikowski,et al.  Asymmetric Heck cyclization route to indolizidine and azaazulene alkaloids: synthesis of (+)-5-epiindolizidine 167B and indolizidine 223AB , 2001 .

[28]  Sandrine Péroche,et al.  A convenient allylsilane-N-acyliminium route toward 5-alkylindolizidines. Diastereoselective synthesis of (±)-indolizidine 167B , 2001 .

[29]  F. A. Davis,et al.  Alkaloid Synthesis Using Chiral δ-Amino β-Ketoesters: A Stereoselective Synthesis of (−)-Lasubine II , 2000 .

[30]  Agami,et al.  An Efficient Access to Enantiomerically Pure Substituted Derivatives of Pipecolic Acid. , 2000, The Journal of organic chemistry.

[31]  Jaehong Lim,et al.  Radical cyclization of β-aminoacrylates: Synthesis of (-)-indolizidine 223AB , 2000 .

[32]  Ratni,et al.  Synthesis of (-)-Lasubine(I) via a Planar Chiral (eta(6)-Arene)Cr(CO)(3)] Complex. , 1999, Organic letters.

[33]  P. Chalard,et al.  Enantioselective synthesis of (−)-indolizidine 167B , 1999 .

[34]  H. Dhimane,et al.  Synthesis of indolizidines (−)-195B, (−)-223AB and (−)-239AB: (2S,5R)-1-[(benzyloxy)carbonyl]-2-methoxycarbonyl-5-(4-pentenyl)pyrrolidine as a versatile chiral building block , 1998 .

[35]  M. Mori,et al.  ATMOSPHERIC NITROGEN FIXATION. SHORT-STEP SYNTHESIS OF MONOMORINE I , 1998 .

[36]  D. Gardette,et al.  Enantioselective synthesis of the quinolizidine alkaloids (+)-myrtine and (−)-epimyrtine , 1998 .

[37]  J. Michael,et al.  An Expeditious Synthesis of the Dendrobatid Indolizidine Alkaloid 167B , 1998 .

[38]  V. Bardot,et al.  Enantioselective synthesis of 2-(2-hydroxyethyl)allylsilanes from chiral β-hydroxyesters , 1997 .

[39]  V. Bardot,et al.  A Facile Synthesis of 2-(2-Hydroxyethyl)allylsilanes , 1996 .

[40]  A. O. Maldaner,et al.  One-Pot Preparation of Quinolizidin-2-one and Indolizidin-7-one Ring Systems. Concise Total Syntheses of (.+-.)-Myrtine, (.+-.)-Lasubine II, and (-)-Indolizidine 223AB , 1995 .

[41]  R. Mayadunne,et al.  Highly diastereoselective formation of substituted indolizidines and quinolizidines by radical cyclization , 1993 .

[42]  A. O. Maldaner,et al.  Tandem N-acyliminium-Michael addition reaction. An efficient total Synthesis of the quinolizidine alkaloids (+/−)-myrtine and (+/−)-lasubine II. , 1993 .

[43]  D. Comins,et al.  Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates. Asymmetric syntheses of the quinolizidine alkaloids, (+)-myrtine, (-)-lasubine I, and (+)-subcosine I , 1992 .

[44]  J. Gramain,et al.  Intramolecular cyclization of allylsilyl substituted N-acyliminium ions. Access to 1- and 2-azabicyclo [X.Y.0]-alkanes. Total synthesis of (±)-mesembrine , 1992 .

[45]  A. Louvet,et al.  Diastereoselective cyclization of allylsilanes on α-acyliminium ions. A new approach to (±)-myrtine and (±)-epimyrtine , 1992 .

[46]  S. Pelletier Alkaloids: Chemical and Biological Perspectives , 1992, Alkaloids: Chemical and Biological Perspectives.

[47]  C. Saliou,et al.  Total Synthesis of (+)-Monomorine I (I) from Chiral Cyclic - Enamino Ester. , 1991 .

[48]  O. Ichihara,et al.  Asymmetric synthesis of R-β-amino butanoic acid and S-β-tyrosine: Homochiral lithium amide equivalents for Michael additions to α,β-unsaturated esters. , 1991 .

[49]  S. Pelletier Alkaloids: Chemical and Biological Perspectives , 1991, Alkaloids: Chemical and Biological Perspectives.

[50]  M. Foley,et al.  A highly stereocontrolled, four-step synthesis of (.+-.)-lasubine II , 1988 .

[51]  W. Speckamp,et al.  Synthesis of (±)-lasubine I , 1988 .

[52]  H. Hiemstra,et al.  Diastereoselective alkylation of the dianion of 5-ethoxy-4(S)-hydroxy-1-isopropyl-2-pyrrolidinone; Synthesis of enantiomerically pure azabicycles , 1987 .

[53]  F. King Synthesis of quinolizidines and indolizidines via an intramolecular Mannich reaction , 1986 .

[54]  H. Hiemstra,et al.  Total synthesis of (±)-anatoxin-a via N-acyliminium intermediates , 1986 .

[55]  I. Karle,et al.  Alkaloids from dendrobatid poison frogs: trans-decahydroquinolines and indolizidines , 1986 .

[56]  J. Phillipson Alkaloids: Chemical and Biological Perspectives, Volume 2 , 1985 .

[57]  M. Reetz,et al.  Stereoselective Addition of Organotitanium Reagents to Carbonyl Compounds , 1985 .

[58]  C. Kibayashi,et al.  Synthesis of (.+-.)-lasubine I and II, and (.+-.)-subcosine I , 1984 .

[59]  C. Hootele,et al.  Myrtine and epimyrtine, quinolizidine alkaloids from vaccinium myrtillus , 1981 .

[60]  D. Netzel,et al.  13C nmr assignments of selected octahydroindolizines , 1979 .

[61]  K. Fuji,et al.  Lythraceous Alkaloids. X. Alkaloids of Lagerstroemia subcostata and L. favriei : A Contribution to the Chemotaxonomy , 1978 .

[62]  C. Hootele,et al.  Structure and absolute configuration of myrtine, a new quinolizidine alkaloid from vacciniun myrtillus. , 1978 .

[63]  J. Wijnberg,et al.  NaBH4 reduction of cyclic imides , 1975 .

[64]  K. Leander,et al.  Studies on orchidaceae alkaloids. XXIX. The absolute configuration of dendroprimine, an alkaloid from Dendrobium primulinum Lindl. , 1972, Acta chemica Scandinavica.

[65]  B. Luening,et al.  Studies on orchidaceae alkaloids. VI. Synthesis and relative configuration of 5,7-dimethyloctahydroindolizines. , 1967, Acta chemica Scandinavica.

[66]  K. Leander,et al.  Studies on Orchidaceae Alkaloids. III. The Alkaloids in Dendrobium primulinum Lindl. and Dendrobium chrysanthum Wall. , 1965 .

[67]  Synlett , 2022 .