Total synthesis of the amaryllidaceae alkaloid (+)-plicamine using solid-supported reagents

In this report we describe in full the total synthesis of the amaryllidaceae alkaloid (+)-plicamine 1 including a model compound study. In both cases the compounds were prepared using solid-supported reagents and scavengers in multi-step sequences of reactions to give materials which required no conventional purification but could be carried on to the next synthetic step.

[1]  M. Mori,et al.  First Asymmetric Total Syntheses of (+)-Crinamine, (−)-Haemanthidine, and (+)-Pretazettine , 1998 .

[2]  H. Perlmutter,et al.  (E,E)- and (E,Z)-1,4-dibenzoyl-1,3-butadiene. Synthesis via Wittig condensation and solid-state photochemistry , 1978 .

[3]  J. van Staden,et al.  Crinum species in traditional and modern medicine. , 2001, Journal of ethnopharmacology.

[4]  S. Ley,et al.  Polymer-supported hypervalent iodine reagents in ‘clean’ organic synthesis with potential application in combinatorial chemistry , 1999 .

[5]  S. Ley,et al.  Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents , 1999 .

[6]  G. Henderson,et al.  Oxidation of Hydroquinones, Catechols, and Phenols using Ceric Ammonium Nitrate and Ammonium Dichromate Coated on Silica: An Efficient and Convenient Preparation of Quinones , 1985 .

[7]  S V Ley,et al.  Synthesis of an array of potential matrix metalloproteinase inhibitors using a sequence of polymer-supported reagents. , 1999, Bioorganic & medicinal chemistry letters.

[8]  M. Ochiai,et al.  Radical oxidation of amides and related compounds with hypervalent tert-butylperoxyiodanes: Synthesis of imides and tert-butylperoxyamide acetals , 1999 .

[9]  M. Hesse,et al.  Two novel dinitrogenous alkaloids from Galanthus plicatus subsp. byzantinus (Amaryllidaceae) , 1999 .

[10]  Y. Kita,et al.  Total synthesis of discorhabdin C : a general aza spiro dienone formation from O-silylated phenol derivatives using a hypervalent iodine reagent , 1992 .

[11]  James D White,et al.  Phenolic oxidative coupling with hypervalent iodine. A synthesis of 6a-epipretazettine , 1983 .

[12]  H. Irie,et al.  Total synthesis of the amaryllidaceae alkaloids, lycorine and zephyranthine , 1979 .

[13]  Four New Amaryllidaceae Alkaloids from Galanthus gracilis andÅ@Galanthus plicatus Subsp. byzantinus , 2001 .

[14]  Y. Obata,et al.  Synthesis and biological evaluation of orally active matrix metalloproteinase inhibitors. , 1997, Bioorganic & medicinal chemistry.

[15]  A. M. Gómez,et al.  Serial Radical Cyclization of Pyranose-Derived Dienes in the Stereocontrolled Synthesis of Densely Functionalized Cyclohexanes. A Route to Woodward's Reserpine Precursor , 1994 .

[16]  C. Ebert,et al.  d-Phenylglycine and d-4-hydroxyphenylglycine methyl esters via penicillin G acylase catalysed resolution in organic solvents , 2000 .

[17]  Y. Bigot,et al.  A Simplified Wittig Synthesis Using a Solid/Liquid Transfer Process. VIII - Specific Behaviour of Methyltriphenylphosphorane During Condensation with Phenolic Aldehydes , 1992 .

[18]  Steven V. Ley,et al.  Clean and efficient synthesis of azo dyes using polymer-supported reagents , 2000 .

[19]  Steven V. Ley,et al.  Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation , 2000 .

[20]  W. Marshall,et al.  SOLID-PHASE SYNTHESIS OF CARBOHYDRATE AND PHOSPHODIESTER MODIFIED 2'-5' OLIGOADENYLATE ANALOGS , 1996 .

[21]  Y. Kita,et al.  Hypervalent iodine oxidation of O-silylated phenol derivatives to azacarbocyclic spirodienones; synthetic approach to the anticancer marine alkaloid, discorhabdin C , 1991 .

[22]  M. Hesse,et al.  Substituenteneinfluss bei der massenspektrometrischen Fragmentierung: Untersuchungen an N‐methyl‐β,β′‐diphenyl‐diäthylaminen. 19. Mitteilung über das massenspektrometrische Verhalten von Stickstoffverbindungen , 1973 .

[23]  E. W. Warnhof,et al.  The Structure and Stereochemistry of Undulatine1,2 , 1960 .

[24]  Y. Kita,et al.  Hypervalent Iodine(III)-Induced Intramolecular Cyclization of α-(Aryl)alkyl-β-dicarbonyl Compounds: A Convenient Synthesis of Benzannulated and Spirobenzannulated Compounds , 2001 .

[25]  M. J. Heeg,et al.  Total Synthesis of (±)-Tazettine , 1998 .

[26]  Steven V. Ley,et al.  A Concise Synthesis of the Natural Product Carpanone Using Solid-Supported Reagents and Scavengers , 2002 .

[27]  Steven V. Ley,et al.  Synthesis of the potent analgesic compound (±)-epibatidine using an orchestrated multi-step sequence of polymer supported reagents , 1999 .

[28]  I R Baxendale,et al.  Polymer-supported reagents for multi-step organic synthesis: application to the synthesis of sildenafil. , 2000, Bioorganic & medicinal chemistry letters.

[29]  S. Ley,et al.  Clean synthesis of α-bromo ketones and their utilisation in the synthesis of 2-alkoxy-2,3-dihydro-2-aryl-1,4-benzodioxanes, 2-amino-4-aryl-1,3-thiazoles and piperidino-2-amino-1,3-thiazoles using polymer-supported reagents , 1999 .

[30]  S. Furusawa,et al.  Therapeutic Activity of Pretazettine, a Narcissus Alkaloid on Rauscher Leukemia: Comparison with Tazettine and Streptonigrin 1 , 1976, Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine.

[31]  Steven V. Ley,et al.  Synthesis of the alkaloids (±)-oxomaritidine and (±)-epimaritidine using an orchestrated multi-step sequence of polymer supported reagents , 1999 .

[32]  A. Persidis High-throughput screening , 1998, Bio/Technology.

[33]  Y. Kita,et al.  Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent: Leading to Galanthamine-Type Amaryllidaceae Alkaloids , 1998 .

[34]  Steven V. Ley,et al.  Total synthesis of the amaryllidaceae alkaloid (+)-plicamine and its unnatural enantiomer by using solid-supported reagents and scavengers in a multistep sequence of reactions. , 2002 .

[35]  N. Nakamura,et al.  Inhibitory effects of Korean plants on HIV‐1 activities , 2001, Phytotherapy research : PTR.

[36]  J. C. Clark,et al.  A new asymmetric transformation of α-amino-acid esters with (+)-tartaric acid , 1976 .

[37]  A. Börner,et al.  β-Alkoxy- and β-Hydroxyalkylphosphanes as Ligands in the Stereoselective Hydrogenation — A Comparison , 1995 .

[38]  J M Pezzuto,et al.  Cytotoxicity of Hymenocallis expansa alkaloids. , 1993, Journal of natural products.

[39]  M. Schwartz,et al.  Intramolecular oxidative phenol coupling. A new method , 1969 .

[40]  E. Kotani,et al.  Intramolecular and intermolecular oxidative coupling reactions by a new iron complex [Fe(DMF)3Cl2][FeCl4] , 1972 .

[41]  Y. Iitaka,et al.  A synthesis of (±)-Δ2-α-Lycoren-7-one, the key intermediate for the total synthesis of (±)-lycorine , 1984 .

[42]  M. Roof,et al.  A mild procedure for etherification of alcohols with primary alkyl halides in the presence of silver triflate , 1994 .

[43]  K. Isobe,et al.  Synthesis of four possible stereoisomers of 1,2-epoxy-3-hydroxyerythrinans: total synthesis of an alkenoid-type erythrinan alkaloid, (±)-erythratidine , 2000 .

[44]  正利 山崎,et al.  ヒガンバナ科アルカロイド, リコリン及びリコリシジノールによる炎症性サイトカイン, TNF-α産生の阻害 , 2001 .

[45]  E. Furusawa,et al.  Therapeutic activity of pretazettine, standard drugs, and the combinations on intraperitoneally implanted Lewis lung carcinoma in mice. , 1983, Chemotherapy.

[46]  G. Gokel,et al.  Host-guest complexation. 11. Survey of chiral recognition of amine and amino ester salts by dilocular bisdinaphthyl hosts , 1978 .

[47]  G. Olah,et al.  Catalysis by solid super acids. 20. Nafion-H catalyzed reductive cleavage of acetals and ketals to ethers with triethylsilane , 1986 .

[48]  S. Furusawa,et al.  Effect of pretazettine and viva-natural, a dietary seaweed extract, on spontaneous AKR leukemia in comparison with standard drugs. , 1988, Oncology.

[49]  H. Fales,et al.  Interconversions of Amaryllidaceae Alkaloids by Sodium and Amyl Alcohol1 , 1958 .

[50]  J. Gramain,et al.  Photochemical Synthesis of Spirocyclohexylisoquinolines, Analogues of (±)-Galanthamine and (±)-Lycoramine , 1997 .

[51]  H. Irie,et al.  Therapeutic activity of pretazettine on Rauscher leukemia: comparison with the related Amaryllidaceae alkaloids. , 1980, Chemotherapy.

[52]  S. Ley,et al.  Clean six-step synthesis of a piperidino-thiomorpholine library using polymer-supported reagents , 1998 .

[53]  Steven V. Ley,et al.  Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents , 1999 .

[54]  G. Çitoǧlu,et al.  Alkaloids of Sternbergia clusiana and their Analgesic Effects , 1996 .

[55]  S. Ley,et al.  Polymer supported reagents in synthesis: preparation of bicyclo[2.2.2] octane derivates via Tandem Michael addition reactions and subsequent combinatorial decoration. , 2000, Journal of combinatorial chemistry.