The 5-Endo-trig Cyclization of D-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxycastanospermine and its 8a-epi-Analogue†

Dhavale, Dilip D.; Jachak, Santosh M.

doi:10.3390/10080893

Cited by 15 publications

(7 citation statements)

References 15 publications

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“…In a further extension, the nitrone 35 was treated with allylmagnesium bromide followed by reduction with zinc in acetic acid to produce a separable mixture of amine diastereomers 48. 15 Applying the aminomercuration-reductive demercuration sequence then afforded the pyrrolidine diastereomers 49, which could in turn be converted into (+)-1-deoxycastanospermine 50 and its 8a-epimer 51 as illustrated.…”

Section: Castanospermine and Related Compoundsmentioning

confidence: 99%

Indolizidine and quinolizidine alkaloids

2008

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This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids. Included in the review are the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from animal sources, including arthropods and amphibians; alkaloids from the genera Polygonatum, Prosopis and Poranthera; phenanthroindolizidine and phenanthroquinolizidine alkaloids; Nuphar alkaloids; lupine alkaloids; and alkaloids from marine sources. 130 references are cited.

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Section: Castanospermine and Related Compoundsmentioning

confidence: 99%

Indolizidine and quinolizidine alkaloids

2008

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“…Physical and spectral data are in accordance with the literature. 64,65 1-Benzyl-2-butylpiperidine (5a). Prepared from the 1-benzyl-6methylsulfanyl-2,3,4,5-tetrahydropyridinium iodide 3 (339 mg, 0.98 mmol) according to the procedure for 2a.…”

Section: ■ Experimental Sectionmentioning

confidence: 72%

Reductive Alkylation of Tertiary Lactams via Addition of Organocopper (RCu) Reagents to Thioiminium Ions

et al. 2017

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A simple procedure for the conversion of tertiary lactams to 2-monoalkylated cyclic amines is described. The reaction sequence involves conversion of a lactam to a thioiminium ion followed by reaction with an organocopper (RCu) reagent and final reduction with triacetoxyborohydride. The reaction is high yielding and shows an excellent functional group tolerance. Its utility is demonstrated by a rapid synthesis of indolizidine 167B. The excellent chemoselectivity of the process, where only monoalkylation products are formed, is rationalized by a mechanism involving the formation of a transient enamine.

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“…[52] It was the sugar residue at the nitrone carbon which mainly governed the stereochemical induction. Again, for nitrone 33 an enhancement of the diastereoselectivity was observed by activating the nitrone with TMSOTf which allowed to perform the reaction at -78ºC; [53] otherwise, the reaction needed to be conducted at higher temperatures and lower selectivities were observed. Cyclic nitrone 34 showed a higher selectivity leading to hydroxylamine 35 in 70% and 92% ds (Scheme 9).…”

Section: Methodsmentioning

confidence: 99%

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

Matute¹,

García‐Viñuales²,

Hayes³

et al. 2016

COS

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This review covers the recent advances in the synthesis of enantiomerically pure hydroxylamines employing nitrones as starting materials. Nucleophilic additions of organometallic reagents to nitrones are the most common way for introducing a hydroxyamino group into carbon skeletons with the concomitant formation of a new carbon-carbon bond. Addition of carbanions derived from enolates, cyanide or fluorinated derivatives allow the preparation of complex structures. Radical additions and, in particular samarium diiodide-mediated reductive coupling of nitrones with carbonyl compounds and α,β-unsaturated esters have also been considered. All these approaches provide efficient methods of preparation of enantiomerically pure hydroxylamienes that are valuable synthetic intermediates. KeywordsHydroxylamines; Nitrones; Organometallics; Mannich; Reductive coupling 2 Graphical Abstract 3

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The 5-Endo-trig Cyclization of D-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxycastanospermine and its 8a-epi-Analogue†

Cited by 15 publications

References 15 publications

Indolizidine and quinolizidine alkaloids

Indolizidine and quinolizidine alkaloids

Reductive Alkylation of Tertiary Lactams via Addition of Organocopper (RCu) Reagents to Thioiminium Ions

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

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