- Total Synthesis of (±)-Pestalachloride C and (±)-Pestalachloride D through a Biomimetic Knoevenagel/Hetero-Diels-Alder Cascade
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A concise total synthesis of (±)-pestalachloride C and (±)-pestalachloride D was achieved through a Knoevenagel/hetero-Diels-Alder cascade reaction to test the nonenzymatic biosynthetic hypothesis of Shao, Wang, and co-workers. The cascade reaction generates a mixture of racemic indano[2,1-c]chromans like those found in the natural products.
- Arredondo, Vanessa,Roa, Daniel E.,Yan, Songyuan,Liu-Smith, Feng,Van Vranken, David L.
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supporting information
p. 1755 - 1759
(2019/03/20)
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- Palladium-catalyzed insertion of N-tosylhydrazones for the synthesis of isoindolines
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Isoindolines are synthesized by palladium-catalyzed coupling reaction of N-(2-iodobenzyl) anilines with α,β-unsaturated N-tosylhydrazones. The reaction has several potential advantages: (1) toleration of a wide range of functional groups, (2) easy to handle and with mild conditions, (3) enriches the isoindoline family, (4) two new bonds form in one step.
- Zhou, Ping-Xin,Luo, Jian-Yi,Zhao, Lian-Biao,Ye, Yu-Ying,Liang, Yong-Min
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supporting information
p. 3254 - 3256
(2013/05/08)
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- Phosphine/palladium-catalyzed syntheses of alkylidene phthalans, 3-deoxyisoochracinic acid, isoochracinic acid, and isoochracinol
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In this study we used sequential catalysis-PPh3-catalyzed nucleophilic addition followed by Pd(0)-catalyzed Heck cyclization-to construct complex functionalized alkylidene phthalans rapidly, in high yields, and with good stereoselectivities (E/Z ratios of up to 1:22). The scope of this Michael-Heck reaction includes substrates bearing various substituents around the alkylidene phthalan backbone. Applying this efficient sequential catalysis, we accomplished concise total syntheses of 3-deoxyisoochacinic acid, isoochracinic acid, and isoochracinol.
- Fan, Yi Chiao,Kwon, Ohyun
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supporting information; experimental part
p. 3264 - 3267
(2012/08/28)
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- An efficient entry to pyrrolo[1,2-b]isoquinolines and related systems through Parham cyclisation
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Aryllithiums generated by lithium-iodine exchange undergo intramolecular cyclisation to give pyrrolo[1,2-b]isoquinolines, in high yields. The best results were obtained when Weinreb or morpholine amides were used as internal electrophiles. The procedure h
- Ruiz, Javier,Ardeo, Ainhoa,Ignacio, Roberto,Sotomayor, Nuria,Lete, Esther
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p. 3311 - 3324
(2007/10/03)
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- Simple and regioselective oxyiodination of aromatic compounds with ammonium iodide and Oxone
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Oxyiodination of aromatic compounds using NH4I and Oxone gives high yields and selectivity. A simple method for the iodination of aromatic compounds using NH4I as the iodine source and Oxone as the oxidant is described.
- Krishna Mohan,Narender,Kulkarni
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p. 8015 - 8018
(2007/10/03)
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- Parham-type cycliacylation with Weinreb amides. Application to the synthesis of fused indolizinone systems
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(Matrix presented) Weinreb amides behave as efficient internal electrophiles in Parham-type cycliacylation reactions. Thus, aryl- and heteroaryllithiums generated by lithium-halogen exchange undergo intramolecular cyclization to give fused indolizinone systems as pyrrolo[1,2-b]isoquinolines, thieno[2,3-f]indolizinones, and pyrrolo[1,2-b]acridinones in high yields.
- Ruiz, Javier,Sotomayor, Nuria,Lete, Esther
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p. 1115 - 1117
(2007/10/03)
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- Carbopalladation of nitriles: Synthesis of benzocyclic ketones and cyclopentenones via Pd-catalyzed cyclization of ω-(2-iodoaryl)alkanenitriles and related compounds
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An efficient procedure for the synthesis of 2,2-disubstituted benzocyclic ketones by intramolecular carbopalladation of nitriles has been developed. The cyclization of substituted 3-(2-iodoaryl)-propanenitriles affords indanones in high yields. The reaction is compatible with a wide variety of functional groups. This methodology has been extended to the synthesis of tetralones and cyclopentenones.
- Pletnev, Alexandre A.,Larock, Richard C.
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p. 9428 - 9438
(2007/10/03)
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- A Convenient Strategy for the Synthesis of 4,5-Bis(o-haloaryl)isoxazoles
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A series of new 1,2-bis(o-haloaryl)ethanones is efficiently prepared and applied to the synthesis of 4,5-bis(o-haloaryl)isoxazoles. Isolation of intermediate hydroxyisoxazolines, which are structurally examined, provides a definitive proof for a heterocyclization mechanism based on an amine exchange process. The isolation and X-ray crystallographic studies of significant side products such as benzamides and triarylpropionitriles are also described.
- Olivera, Roberto,SanMartin, Raul,Dominguez, Esther,Solans, Xabier,Urtiaga, Miren Karmele,Arriortua, Maria Isabel
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p. 6398 - 6411
(2007/10/03)
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- Synthesis of ring-halogenated 3,4-dimethoxyphenylethanolamine derivatives: New β-adrenoceptor antagonists
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A series of ring-halogenated derivatives (bromo and iodo) of [2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]isopropylamine and [2-(3,4-dimethoxyphenyl)-2-methoxyethyl]isopropylamine was synthesized from benzaldehyde derivatives, via (halo-3,4-dimethoxyphenyl)ethylene oxide compounds. The compounds were tested as β-adrenoceptor antagonists on isolated guinea-pig tracheal (β2-adrenoceptors) and guinea-pig atrial (β1-adrenoceptors) muscle strips. Compounds halogenated in the 2-and 5-positions of the aromatic ring are potent β2-adrenoceptor antagonists, whereas halogenation of the 6-position of the aromatic ring leads to compounds which are weak β-adrenoceptor antagonists. β1-Selective drugs of very low potency were obtained when the β-hydroxyl group was replaced by a methoxy group.
- Venter, Daniel P.,Langenhoven, Jan H.
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- The asymmetric synthesis of aryltetralin lignans: (-)-isolariciresinol dimethyl ether and (-)-deoxysikkimotoxin
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The total asymmetric syntheses of (-)-isolariciresinol dimethyl ether (6) and (-)-deoxysikkimotoxin (7) have been carried out, in an attempt to exploit a synthetic strategy recently developed for the synthesis of (-)-deoxypodophyllotoxin (1, R1 = -CH2-, Ar = 3,4,5-trimethoxyphenyl). In so doing, a generalized method for the synthesis of aryltetralin lignans has been developed that should be applicable to a variety of substitution patterns and stereochemistries. A one-pot, 100% regio-selective reduction-lactonization procedure has been developed for the conversion of the ester 18b to (-)-deoxysikkimotoxin, which gave 93% isolated yield in that step.
- Coltart, Don M.,Charlton, James L.
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- A New Approach to the Synthesis of Peltogynoids, Natural Isochromenochromenes
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The (+/-)-trimethyl ether of the unusual isochromenochromene peltogynol 1 (R = OMe) and its ring skeleton 1 (R = H) have been synthesized via 6-endo intramolecular cyclisation of the radicals derived from the 3-(o-iodobenzyloxy)chromones 17 (R = OM
- Ahmad-Junan, S. Asiah,Whiting, Donald A.
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p. 675 - 678
(2007/10/02)
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- Anionic Fries Rearrangements of Esters of ortho-Iodobenzyl Alcohols: Rapid Routes to Oestrone Methyl Ether and Its 9β Epimer, and Aryl Naphthalide Lignans
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A fast, general, low-temperature rearrangement of ortho-iodobenzyl esters, triggered by lithium-iodine exchange, leads to isobenzofurans which are intercepted in situ by inter and intramolecular Diels-Alder (IMDA) reactions to produce a variety of carbocycles including natural lignans and steroids.
- Horne, Stephen,Rodrigo, Russell
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p. 164 - 166
(2007/10/02)
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- Naturally Occuring Dibenzofurans. Part 9. A Convenient Synthesis of Phthalides: The Synthesis of Methyl Di-O-methylporphyrilate
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A convenient synthesis of phthalides from o-halogenobenzyl alcohols is described.This method is then applied to the synthesis of methyl di-O-methylporphyrilate (methyl 1,3-dihydro-4,10-dimethoxy-8-methyl-3-oxoisobenzofuro
- Sargent, Melvyn V.
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p. 231 - 236
(2007/10/02)
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