A Route to “all‐cis” 2‐Methyl‐6‐Substituted Piperidin‐3‐ol Alkaloids from syn‐(2R,1′S)‐2‐(1‐Dibenzylaminomethyl)epoxide: Rapid Total Synthesis of (+)‐Deoxocassine

Geant, Pierre‐Yves; Martínez, Jean; Salom‐Roig, Xavier J.

doi:10.1002/ejoc.201101333

Cited by 8 publications

(5 citation statements)

References 33 publications

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“…Subsequent lactam formation gave 152 - 5 in 72% overall yield. This one-pot reductive amination strategy was also employed in the syntheses of (−)-lycojaponicumin C, (+)-1- epi -castanospermine, (+)-deoxocassine, and (+)-dihydropinidine and (−)-pinidinone …”

Section: Reduction Of Imines and Enamines (Figure )mentioning

confidence: 99%

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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The main objective of this review is to provide a comprehensive survey of methods used for stereoselective construction of carbon-nitrogen bonds during the total synthesis of nitrogen-containing natural products that have appeared in the literature since 2000. The material is organized by specific reaction in order of decreasing number of applications in natural product synthesis. About 800 total syntheses of natural products with stereogenic carbon-nitrogen bonds described since 2000 have been reviewed.

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Section: Reduction Of Imines and Enamines (Figure )mentioning

confidence: 99%

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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“…In an earlier study, we reported on the synthesis of α-( S )-dibenzylamino ketones from nonracemic α-bromo-α′-( R )-sulfinyl ketones optically pure only at the sulfur atom ( 1 , Scheme ) via combined in situ substitution–epimerization in a so-called Dynamic Kinetic Resolution (DKR). During the course of that study, a serendipitous discovery was made when the 55:45 epimeric mixtures 1a and 1b , stored for 12 h at 0 °C, precipitated.…”

mentioning

confidence: 99%

Crystallization-Induced Diastereomer Transformation of α-Bromo α′-Sulfinyl Ketones. Diastereodivergent Synthesis of (+)-α-Conhydrine and (−)-β-Conhydrine

2021

Self Cite

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Crystallization-Induced Diastereomer Transformation (CIDT) of α-bromo-α′-(R)-sulfinylketones is reported. This process provides not readily accessible enantiopure stereolabile αbromoketones, which after diastereoselective carbonyl group reduction lead to the corresponding highly value-added anti and syn-bromohydrins with excellent diastereoselectivities. As an application, a diastereodivergent synthesis of enantiopure hemlock alkaloid (+)-α-conhydrine and its diastereomer (−)-β-conhydrine is also described.

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“…The physical data were identical in all respect to that previously reported. [9] (E)-6-Bromohex-2-ene (DH02-273-1)…”

Section: (E)-2-(butan-2-ylidene)-11-dimethylhydrazine (Dh02-267-1)mentioning

confidence: 99%

Palladium(II)-Catalyzed C(sp3)–H Activation of N,O-Ketals towards a Method for the β-Functionalization of Ketones

Ho¹,

Calleja²,

Gaunt

2019

Synlett

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A method for the formal β-functionalization of aliphatic ketones via a palladium-catalyzed sp3 C–H activation pathway is reported. An N,O-ketal directs an aliphatic C–H carbonylation to form γ-lactams which upon hydrolysis generate γ-keto carboxylic acids. This C–C bond-forming reaction is tolerant of a range of functional groups, enabling the synthesis of a range of synthetically important building blocks. Furthermore, the concepts underlying this transformation have also enabled the development of a related C–H alkenylation process to highly functionalised heterocycles.

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A Route to “all‐cis” 2‐Methyl‐6‐Substituted Piperidin‐3‐ol Alkaloids from syn‐(2R,1′S)‐2‐(1‐Dibenzylaminomethyl)epoxide: Rapid Total Synthesis of (+)‐Deoxocassine

Abstract: A general strategy leading to the synthesis of two cis-2-methyl-6-substituted piperidin-3-ols is described. syn-(2R,1ЈS)-2-(1-Dibenzylaminomethyl) epoxide (13) was used as common building block. The key step involved oxirane ring opening of 13 by the nucleophilic lithium aza-enolate of

Cited by 8 publications

References 33 publications

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

Crystallization-Induced Diastereomer Transformation of α-Bromo α′-Sulfinyl Ketones. Diastereodivergent Synthesis of (+)-α-Conhydrine and (−)-β-Conhydrine

Palladium(II)-Catalyzed C(sp3)–H Activation of N,O-Ketals towards a Method for the β-Functionalization of Ketones

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