Stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine, and (+)-sedamine through a common intermediate

Satyalakshmi, Gandham; Suneel, Kanaparthy; Shinde, Digambar Balaji; Das, Biswanath

doi:10.1016/j.tetasy.2011.06.011

Cited by 19 publications

(8 citation statements)

References 55 publications

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“…It seems that the nucleophilic nature of the nitrogen atom in the NO bond of isoxazolidine 11 deactivates the metathesis catalyst. This problem was previously encountered by Bates and co‐workers in their total synthesis of sedamine 3d. Therefore, an alternative approach was undertaken, in which the NO bond was first cleaved to give the amino alcohol 13 (10:1 mixture of diastereomers), which was then reprotected as the cyclic carbamate 14 (10:1 mixture of diastereomers) using triphosgene (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Stereodivergent Synthesis of Piperidine Alkaloids by Ring‐Rearrangement Metathesis/Reductive Lactam Alkylation of Nitroso Diels–Alder Cycloadducts

Vincent

Karila

Khalil

et al. 2013

Chemistry A European J

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A general methodology for the stereoselective synthesis of 2-(2-hydroxyalkyl)piperidine alkaloids by ring-rearrangement metathesis of nitroso Diels-Alder cycloadducts is reported. The approach is illustrated by the formal synthesis of porantheridine and the total synthesis of andrachcinidine through a diastereodivergent allylation of an N-alkoxy bicyclic lactam. The asymmetric synthesis of the latter alkaloid provides new insights into the configurational stability of cycloadducts between chloronitroso reagents and cyclopentadiene.

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Section: Resultsmentioning

confidence: 99%

Stereodivergent Synthesis of Piperidine Alkaloids by Ring‐Rearrangement Metathesis/Reductive Lactam Alkylation of Nitroso Diels–Alder Cycloadducts

Vincent

Karila

Khalil

et al. 2013

Chemistry A European J

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“…), such as desoxoprosophylline, cassine, pinidinone, deoxyfebrifugine and norallosedamine, among others . The synthesis of other related alkaloids such as sedamine and 5‐hydroxy sedamine, halosaline and pelletierine could also be easily envisaged by exploiting the reactivity of such vinylogous amides.…”

Section: Alkaloids From Vinylogous Amidesmentioning

confidence: 99%

From synthetic control to natural products: a focus on N‐heterocycles

Prandi

Occhiato

2019

Pest Management Science

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Natural products containing a N‐heterocycle motif are widespread in nature and medicinal plants, in particular, have proved to be a source of almost unlimited N‐derived structures with high molecular diversity. Because of their intrinsic potential for use in both biomedical and agricultural applications, there is a general need for new compounds and for the synthesis of ‘natural‐inspired’ analogues. Importantly, transition of a natural product from discovery to a ‘market lead’ is associated with an increasingly challenging demand for more of the compound, which cannot be met by isolation from natural plant sources, often due to low extraction yields and uneven availability of the plant source itself. Synthesis remains the most reliable approach to provide valuable products for the market. In this review, a comprehensive overview of our contribution to synthetic access to N‐derived natural products is given. Major strengths of the proposed methodologies are discussed critically. © 2019 Society of Chemical Industry

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“…Some research groups took into account the enantioselective synthesis of 1 or aldehyde 2 ; an early strategy was established on intermolecular nitrone cycloadditions to chiral allyl ethers [ 18 , 19 ] obtaining benzyl carbamate ( N -Cbz) 2 . Asymmetric allylation was the next synthetic tool using a chiral auxiliary [ 20 , 21 ]; a synthetic sequence involving a Maruoka asymmetric allylation with a chiral catalyst [ 22 ] was successful in obtaining N -Boc 2 . Recently, a straightforward organocatalyzed intramolecular aza-Michael reaction accomplished the synthesis of either N -Boc or N -Cbz 2 in high enantiomeric excess (e.e.)…”

Section: Enantiopure 2-piperidineethanol: Resolution Vermentioning

confidence: 99%

Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis

Perdicchia

Christodoulou

Fumagalli

et al. 2015

IJMS

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2-Piperidineethanol (1) and its corresponding N-protected aldehyde (2) were used for the synthesis of several natural and synthetic compounds. The existence of a stereocenter at position 2 of the piperidine skeleton and the presence of an easily-functionalized group, such as the alcohol, set 1 as a valuable starting material for enantioselective synthesis. Herein, are presented both synthetic and enzymatic methods for the resolution of the racemic 1, as well as an overview of synthesized natural products starting from the enantiopure 1.

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Stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine, and (+)-sedamine through a common intermediate

Cited by 19 publications

References 55 publications

Stereodivergent Synthesis of Piperidine Alkaloids by Ring‐Rearrangement Metathesis/Reductive Lactam Alkylation of Nitroso Diels–Alder Cycloadducts

Stereodivergent Synthesis of Piperidine Alkaloids by Ring‐Rearrangement Metathesis/Reductive Lactam Alkylation of Nitroso Diels–Alder Cycloadducts

From synthetic control to natural products: a focus on N‐heterocycles

Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis

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