Enantiodivergent Synthesis of Both Enantiomers of Marine Alkaloids Haliclorensin and Isohaliclorensin, a Constituent of Halitulin

Zheng, Jian‐Feng; Jin, Lihua; Huang, Pei‐Qiang

doi:10.1021/ol049887k

Cited by 39 publications

(18 citation statements)

References 27 publications

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“…Notably, all of the 6‐membered azacycles underwent ring expansions with remarkable stereoselectivities through stereodefined chair‐like transition states, such as 2 and 5 . This method was also applied to the synthesis of isohaliclorensin and haliclorensin …”

Section: Acr‐induced Ring‐expansion Strategies For the Synthesis Of Mmentioning

confidence: 99%

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Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

2017

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The aza-Claisen rearrangement,a lso known as the 3-aza-Coper earrangement, has attracted significant attention because it can be used as ac omplimentarym ethodt o access ad iverse range of useful organic molecules. The presence of an itrogen atom at the 3-position enables the tethering of various-sized azacycles, thereby giving ring-expansion strategiest hat take advantage of the aza-Claisen rearrangementadistinct advantage comparedt oo ther [3,3]-sigmatropic rearrangements. Recent advances in aza-Claisen rearrangements have facilitatedo therwise-inaccessible ring expansions in ah ighly stereoselective manner. The utility of aza-Claisen-rearrangement-induced ring-expansion strategies has been exemplified in the synthesis of ad iverse range of naturalp roducts. This Focus Review summarizes recent advancesi na za-Claisen-rearrangement-induced ring-expansion strategy, in particular applicationsi nt he synthesis of bioactive alkaloids.

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Section: Acr‐induced Ring‐expansion Strategies For the Synthesis Of Mmentioning

confidence: 99%

“…It is well‐known that 6‐membered azacycles with defined stereochemistry are well‐suited for ACR reactions . A strained variant, such as the benzene‐ring‐fused azacycle dihydroisoquinoline, was also shown to be suitable for the ACR, as shown in Scheme .…”

Section: Acr‐induced Ring‐expansion Strategies For the Synthesis Of Mmentioning

confidence: 99%

Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

2017

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“…In another route, enantiopure ( S )‐ and ( R )‐coniceine analogues were prepared through four‐step reactions. Therefore, treatment of oxazolopyridine ent ‐ 51 with vinyl magnesium bromide in THF yielded vinyl piperidines 198 / 198 ′ in a ratio of 1:7 in a yield of 94% as a mixture of diastereomers . Several reports described the axial attack of the Grignard reagent to iminium intermediate indicating the stereochemistry of the major observed isomer 198.…”

Section: Reactionsmentioning

confidence: 99%

Reactivity and stereoselectivity of oxazolopyridines with a ring‐junction nitrogen atom

Monier

Abdel-Latif

El‐Mekabaty

et al. 2019

Journal of Heterocyclic Chem

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The present study demonstrates a synopsis of the scientific researches reported on the different reactions of oxazolo[3,2‐a]pyridines, besides the preparation of significant fused heterocycles up till now. The different main sections that described the reactivity of the inspected analogues include stereoselective alkylation, reactions involved oxazolidine ring, synthesis of polycyclic systems, indole alkaloids, and alkyl amines. The stereochemical selectivity of oxazolopiperidone lactams is studied, in which the configuration of the stereocenter C8a and substituents at the C8 and C8a effect on the stereoselectivity. On the other hand, the synthetic consequence of the alkylation products provides diverse routes for the synthesis of substituted enantiopure piperidines that are used for the synthesis of natural products, for example, (−)‐rhazinilam, (+)‐eburnamonine, (+)‐aspidospermidine, indole alkaloids such as dihydrocleavamine, nor‐20‐epiuleine, (+)‐dasycarpidone, (+)‐uleine, indoloquinolizidine, (+)‐dihydrocorynantheine, (−)‐dihydrocorynantheol, and indolizines, eg, octahydroindolizines, monomorine I, (−)‐S‐coniceine, and (−)‐R‐coniceine.

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“…Final deprotection by hydrogenation gave chiral 2-substituted piperidines 256 (Scheme 91) [183]. A similar synthesis starting from (R)-2-phenylglycinol led to the opposite enantiomer of 256 [184].…”

Section: Piperidinesmentioning

confidence: 99%

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

Beagle

2015

Topics in Heterocyclic Chemistry

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Application of benzotriazole methodology for the preparation of nitrogen-containing heterocyclic compounds is summarized in this review. The characteristic advantages of benzotriazole are first briefly considered followed by an overview of its use in the synthesis of heterocycles organized by the ring size. Finally, the use of benzotriazole in the synthesis of bicyclic systems is showcased in only selected examples.

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Enantiodivergent Synthesis of Both Enantiomers of Marine Alkaloids Haliclorensin and Isohaliclorensin, a Constituent of Halitulin

Cited by 39 publications

References 27 publications

Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

Reactivity and stereoselectivity of oxazolopyridines with a ring‐junction nitrogen atom

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

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