Formal synthesis of (±)-indolizidine 209B

Liou, Bo-Sian; Jhang, Ruei-Fong; Chou, Shang‐Shing P.

doi:10.1016/j.tet.2014.08.015

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Cited by 6 publications

(1 citation statement)

References 49 publications

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“…The mixture was treated with HBr [34] to give the completely isomerized ketone (±)-6. The yield from these two steps, desilylation-epimerization, was 66%.…”

Section: Bnomentioning

confidence: 99%

A Simple Entry to the 5,8-Disubstituted Indolizidine Skeleton via Hetero Diels-Alder Reaction

Rodríguez-Caro,

Afonso,

Palenzuela

2023

Molecules

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The 5,8-disubstituted indolizidines are the largest family of indolizidines isolated from the skin of amphibians. These compounds exhibit interesting biological activities such as noncompetitive blockers of nicotinic receptors. In this paper, we present a short, simple, and general synthesis of these alkaloids based on the hetero Diels–Alder reaction between suitable monoactivated dienes and Δ1-pyrroline as the dienophile. The selectivity of the process is explained based on computational studies. Concise synthesis of the indolizidine alkaloid 181B from a hetero Diels–Alder reaction was accomplished in four steps.

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“…The mixture was treated with HBr [34] to give the completely isomerized ketone (±)-6. The yield from these two steps, desilylation-epimerization, was 66%.…”

Section: Bnomentioning

confidence: 99%

A Simple Entry to the 5,8-Disubstituted Indolizidine Skeleton via Hetero Diels-Alder Reaction

Rodríguez-Caro,

Afonso,

Palenzuela

2023

Molecules

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ChemInform Abstract: Formal Synthesis of (.+‐.)‐Indolizidine 209B.

2015

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Indium‐promoted Conversion of Allylic Bromide to Alcohol Moiety and Synthesis of Pipermethystine Skeletons

Liou

Chou

2016

J Chinese Chemical Soc

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Dihydropyridone bromide (2) was converted to the corresponding alcohol (1) by reaction with indium in air or with indium followed by treatment with a sulfonyloxaziridine. The alcohol (1) was transformed in four steps to a phenylsulfone‐substituted pipermethystine derivative (10). Reductive cleavage of the phenylsulfone did not yield the pipermethystine natural product. Several new pyridone derivatives were synthesized.

show abstract

Formal synthesis of (±)-indolizidine 209B

Cited by 6 publications

References 49 publications

A Simple Entry to the 5,8-Disubstituted Indolizidine Skeleton via Hetero Diels-Alder Reaction

A Simple Entry to the 5,8-Disubstituted Indolizidine Skeleton via Hetero Diels-Alder Reaction

ChemInform Abstract: Formal Synthesis of (.+‐.)‐Indolizidine 209B.

Indium‐promoted Conversion of Allylic Bromide to Alcohol Moiety and Synthesis of Pipermethystine Skeletons

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