Practical and Highly Regio- and Stereoselective Synthesis of 2-Substituted Dihydropyridines and Piperidines:  Application to the Synthesis of (−)-Coniine

Charette, André B.; Grenon, M.; Lemire, Alexandre; Pourashraf, Mehrnaz; Martel, Jonathan

doi:10.1021/ja017136x

Cited by 167 publications

(67 citation statements)

References 7 publications

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“…These syntheses required a total of 19 steps and proceeded in 2% overall yield. The Charette group started synthesis of ent-lepadin B with a diastereoselective 1,2-addition of methyl magnesium bromide to the pyridine adduct with the L-valine derived chiral auxiliary 76 [30,31]. Diastereoselective Diels-Alder reaction with methyl acrylate set the next three stereocenters.…”

Section: Synthetic Effortsmentioning

confidence: 99%

Stereocontrolled construction of decahydro quinoline ring systems: the case of lepadin alkaloids (Review)

Pelšs

Koskinen

2013

Chem Heterocycl Comp

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In this review the marine derived decahydroquinoline alkaloid chemistry and biology is described. A proposal is made for the biosynthetic relationships between acyclic and cyclic C-18 amino alcohol natural products.Keywords: amino alcohols, decahydroquinolines, asymmetric synthesis, biosynthesis, total synthesis. Decahydroquinoline (DHQ) alkaloids are unique natural products that can be divided into three distinct sets. The first group (more than 50 members) of these alkaloids are simple 2,5-disubstituted DHQs isolated from dart poison frogs and ants with the parent member being alkaloid cis-195A, also known as pumiliotoxin C [1]. These diverse cis-or trans-fused decahydroquinolines are equipped with various short alkyl and alkenyl side chains. The structurally related but biologically different lepadins 1-8 (Fig. 1) are on the other hand marine alkaloids isolated from three distinct ascidians: Clavelina lepadiformis (found in the North Sea), Didemnum, and Aplidium tabascum (both found in the Great Barrier Reef) [2][3][4][5]. The third group consists of more complex polycyclic alkaloids that besides the DHQ ring system, can contain several other heterocyclic ring systems fused into one molecule. Representative members of this group are gephyrotoxin and Lycopodium alkaloids [6,7]. This review will focus solely on the second group of DHQ alkaloids which, as distinct from the other two groups of DHQ-containing alkaloids, have not been reviewed in full so far [8]. Lepadin alkaloids differ from dendrobatin frog alkaloids in additional oxygenation at position 3, where the substituent may be a hydroxy or acyloxy group, as well as having eight-carbon long side chains of variable oxidation level at position 5 of the DHQ ring. There are three stereochemical groups of lepadins, each derived from distinct tunicate species (Fig. 1). Lepadin F is an exception, being present in both ascidians from the Great Barrier Reef. Lepadins possess some interesting biological activities: lepadins A and B -cytotoxicity against cancer cell lines, lepadins D-F -antiplasmodal and antitrypanosomal activity. Lately, lepadin B together with pictamine was found to block neuronal nicotinic acetylcholine receptors α4β2 and α7. However, the availability of only small quantities of these natural products has precluded further studies on the development into potential leads for nicotinic based therapies [9].

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Section: Synthetic Effortsmentioning

confidence: 99%

Stereocontrolled construction of decahydro quinoline ring systems: the case of lepadin alkaloids (Review)

Pelšs

Koskinen

2013

Chem Heterocycl Comp

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“…[1][2][3][4] Research into their biological and synthetic applications 5 has led to several methods for preparing them. [6][7][8][9][10] For example, Wender et al reported rhodium-catalyzed aza-[5+2] cycloaddition of cyclopropylimine and alkynes, 6 while Ogoshi et al used nickel catalysis to achieve oxidative cyclization of an imine and alkynes (Scheme 1, eq 1).…”

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confidence: 99%

Rhodium-catalyzed [2+2+2] cycloaddition reactions of terminal alkynes with N -sulfonyl ketimines

Zhang

Dong

2015

Tetrahedron Letters

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“…Dihydropyridines have been recognized as versatile synthetic intermediates [2] that provide access to a variety of heterocycles such as piperidines (by reduction) [3] and pyridines (by oxidation). [4] Considerable efforts have been directed toward the development of new and efficient methodologies for the synthesis of 1,2-dihydropyridines.…”

mentioning

confidence: 99%

“…However, only a 34% yield of the desired compound 6-2a was obtained when the same conditions were used. In search of more effective conditions, we screened the combinations of AuPPh 3 Cl with different silver catalysts and found AgBF 4 gave the best result (69% yield). Additionally, AuPPh 3 Cl/AgOTf failed to afford the target compound, while AuPPh 3 Cl/AgNTf 2 gave the product in 39% yield (Scheme 4).…”

mentioning

confidence: 99%

“…In summary, we have reported our preliminary results on gold-catalyzed tandem reactions for the synthesis of substituted 1,2-dihydropyridines from propargyl vinyl ethers or allenic vinyl ethers and primary amines via gold-catalyzed [3,3]-sigmatropic rearrangement/isomerization/amine condensation/6p-aza-electrocyclization. 2,4-Dienals are the key intermediates in these two tandem reactions.…”

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confidence: 99%

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Synthesis of Substituted 1,2‐Dihydropyridines from Propargyl Vinyl Ethers and Allenic Vinyl Ethers by Gold‐Catalyzed Claisen Rearrangement and 6π‐Aza‐electrocyclization

et al. 2010

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An efficient synthetic method was developed for the construction of substituted 1,2-dihydropyridines by gold-catalyzed tandem reactions. The key intermediates 2,4-dienals were generated from propargyl vinyl ethers or allenic vinyl ethers with gold catalysts. These two reactions involved the process of gold-catalyzed [3,3]-sigmatropic rearrangement/isomerization/amine condensation/6p-aza-electrocyclization.

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Practical and Highly Regio- and Stereoselective Synthesis of 2-Substituted Dihydropyridines and Piperidines: Application to the Synthesis of (−)-Coniine

Cited by 167 publications

References 7 publications

Stereocontrolled construction of decahydro quinoline ring systems: the case of lepadin alkaloids (Review)

Stereocontrolled construction of decahydro quinoline ring systems: the case of lepadin alkaloids (Review)

Rhodium-catalyzed [2+2+2] cycloaddition reactions of terminal alkynes with N -sulfonyl ketimines

Synthesis of Substituted 1,2‐Dihydropyridines from Propargyl Vinyl Ethers and Allenic Vinyl Ethers by Gold‐Catalyzed Claisen Rearrangement and 6π‐Aza‐electrocyclization

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