(3S,4R)-3,4-Dihydroxy-N-alkyl-<scp>l</scp>-homoprolines: synthesis and computational mechanistic studies

Freitas, David S.; Sousa, Cristina E. A.; Parente, Joana Filipa; Drogalin, Artem; Fortes, A. Gil; Cerqueira, Nuno M. F. S. A.; Alves, M. I. Caetano

doi:10.1039/c9ob02141h

Org. Biomol. Chem.

2019

DOI: 10.1039/c9ob02141h

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(3S,4R)-3,4-Dihydroxy-N-alkyl-l-homoprolines: synthesis and computational mechanistic studies

David S. Freitas

Cristina E. A. Sousa

Joana Filipa Parente

et al.

Abstract: This is the first synthetic report of (3S,4R)-dihydroxy-N-alkyl-l-homoprolines described so far.

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2022

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Concise Synthesis of (S)-7-Hydroxy-5-aza-8a-epi-d-swainsonine from a d-Erythrose Derivative

Sousa¹,

Salgueiro²,

Alves³

2022

Synthesis

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A five-step synthesis of (S)-7-hydroxy-8a-epi-5-aza-swainsonine was accessed in good overall yield from readily available D-erythrosyl benzylidene acetal 1,3-butadiene. The key step of the reaction sequence is a full stereoselective Diels-Alder cycloaddition between the diene and dienophile: diethyl azodicarboxylate (DEAD)/ di- t-butyl azodicarboxylate (DBDA). Cycloadducts were further transformed into the title 5-aza-indolizidine. Optimized procedures were obtained for the synthesis of intermediates and products.

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Concise Synthesis of (S)-7-Hydroxy-5-aza-8a-epi-d-swainsonine from a d-Erythrose Derivative

Sousa¹,

Salgueiro²,

Alves³

2022

Synthesis

View full text Add to dashboard Cite

show abstract

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(3S,4R)-3,4-Dihydroxy-N-alkyl-l-homoprolines: synthesis and computational mechanistic studies

Abstract: This is the first synthetic report of (3S,4R)-dihydroxy-N-alkyl-l-homoprolines described so far.

Cited by 1 publication

References 40 publications

Concise Synthesis of (S)-7-Hydroxy-5-aza-8a-epi-d-swainsonine from a d-Erythrose Derivative

Concise Synthesis of (S)-7-Hydroxy-5-aza-8a-epi-d-swainsonine from a d-Erythrose Derivative

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