A Practical Synthesis of (±)-α-Isosparteine from a Tetraoxobispidine Core

Blakemore, Paul R.; Kilner, Colin A.; Norcross, Neil R.; Astles, Peter C.

doi:10.1021/ol0519184

Cited by 27 publications

(20 citation statements)

References 25 publications

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“…30,31 The analytical results were in agreement with their respective formulas. Ligand precursors 1-4 were obtained by condensation reaction between the substituted salicylaldehyde and the corresponding tetramine by a four-step synthesis.…”

Section: Ligand Synthesissupporting

confidence: 80%

“…30,31 Compound I: A stirred mixture of dimethyl malonate and paraformaldehyde at 60 C was treated with 10 wt% KOH in MeOH (10 mL) with stirring for 14 h. Then, the mixture was cooled to RT and shaken with H 2 O (100 mL). 30,31 Compound I: A stirred mixture of dimethyl malonate and paraformaldehyde at 60 C was treated with 10 wt% KOH in MeOH (10 mL) with stirring for 14 h. Then, the mixture was cooled to RT and shaken with H 2 O (100 mL).…”

Section: Synthesis Of Compounds I and Iimentioning

confidence: 99%

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Highly stereoselective bimetallic complexes for lactide and ε-caprolactone polymerization

Pang

Duan

et al. 2014

RSC Adv.

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A series of Schiff-base compounds containing bimetallic ligands and two aluminum centers have been synthesized and characterized by 1 H, 13 C NMR and elemental analysis. These compounds could be successfully used as catalysts for the polymerization of rac-lactide and 3-caprolactone. The polylactides (PLAs) prepared with these compounds were highly isotactic enriched (P m ¼ 0.97). The nature and steric hindrance of the ligands coordinated to the central metal ions remarkably influenced the polymer properties. Kinetic studies revealed that the polymerization was first order with respect to each of these compounds and lactide/caprolactone monomers. All the polymerizations were living, with good molecular weight control and relatively narrow molar mass distributions.Scheme 1 Synthetic pathway for the preparation of ligands and complexes.

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Section: Ligand Synthesissupporting

confidence: 80%

Section: Synthesis Of Compounds I and Iimentioning

confidence: 99%

Highly stereoselective bimetallic complexes for lactide and ε-caprolactone polymerization

Pang

Duan

et al. 2014

RSC Adv.

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“…Therefore, a practical stereocontrolled entry into the sparteine core structure would contribute to exo-ending the versatility of existing asymmetric methods. An elegant approach was detailed in 2005 by Blakemore et al who identified tetraoxobispidine (260) as a synthetically versatile scaffold, which could be readily prepared starting from a Knoevenagel condensation of dimethyl malonate (258) with paraformaldehyde (Scheme 2.57) [85]. The intermediate was directly treated with ammonia (259), followed by cyclization and subsequent double allylation, to provide the key intermediate 260.…”

Section: Indolizidine Alkaloidsmentioning

confidence: 99%

Natural Products Containing Medium‐Sized Nitrogen Heterocycles Synthesized by Ring‐Closing Alkene Metathesis

Broek

Meeuwissen

Delft

et al. 2010

Metathesis in Natural Product Synthesis

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The formation of carbon-carbon bonds is a crucial issue in organic synthesis. Out of all methodologies available, the metathesis reaction has, over the past decade, evolved as one of the most useful tools in this field to rapidly construct the skeleton of carba-and heterocyclic molecules [1]. Key step of the metathesis reaction entails the metal-catalyzed redistribution of two carbon-carbon double bonds by a scission-recombination process [2]. Among various applications of the metathesis reaction, ring-closing metathesis (RCM) has emerged as one of the most powerful tools for the construction of natural and unnatural cyclic compounds (Scheme 2.1) [3]. Other types of metathesis reactions developed so far include cross-metathesis (CM), ring-opening metathesis (ROM), ring rearrangement metathesis (RRM, combining ROM with RCM in a tandem sequence), and ene-yne metathesis [3].The metathesis reaction has already been used for several decades in polymer chemistry for ring-opening metathesis polymerization (ROMP) [4]. Only since the development of well-defined molybdenum and ruthenium carbene complexes by Schrock [5] and Grubbs [6] in 1990 and 1992, respectively, an explosion of their application in organic synthesis has been witnessed. Initially, it was demonstrated that the Schrock catalyst [Mo]-I could serve as a homogeneous catalyst for olefin RCM [7]. Unfortunately, metal carbene complex [Mo]-

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“…[3,4] This type of propanes are usually prepared via a Knoevenagel condensation reaction resulting in symmetrical compounds with identical electron-withdrawing groups. However, non-symmetrical 1,1,3,3-tetrasubstituted propanes can be obtained by a Michael addition of an activated methylene compound to a Knoevenagel adduct.…”

Section: Introductionmentioning

confidence: 99%

Study on the Pd/C‐Catalyzed (Retro‐)Michael Addition Reaction of Activated Methylene Compounds to Electron‐Poor Styrenes

2010

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A Practical Synthesis of (±)-α-Isosparteine from a Tetraoxobispidine Core

Cited by 27 publications

References 25 publications

Highly stereoselective bimetallic complexes for lactide and ε-caprolactone polymerization

Highly stereoselective bimetallic complexes for lactide and ε-caprolactone polymerization

Natural Products Containing Medium‐Sized Nitrogen Heterocycles Synthesized by Ring‐Closing Alkene Metathesis

Study on the Pd/C‐Catalyzed (Retro‐)Michael Addition Reaction of Activated Methylene Compounds to Electron‐Poor Styrenes

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