Concise and Gram-Scale Total Synthesis of Lansiumamides A and B and Alatamide

Lin, Ran; Lin, Xi; Qian, Su; Guo, Baochun; Huang, Yanqin; Ouyang, Mi; Song, Liyan; Xu, Hui

doi:10.3390/molecules24203764

Cited by 4 publications

(1 citation statement)

References 23 publications

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“…Alatamide ( 38 b ) for instance, an amide derived from β ‐phenylethylamine [18,20] could be prepared through a facile two‐step approach in moderate yield as a diastereoisomeric mixture ( E / Z =9:1). Similarly, Lansiunamide A ( 39 b ) and Lansamide I ( 40 b ), two naturally occurring cinnamamides, [21b,22] were prepared following a two‐step synthetic scheme, hereby circumventing tedious total synthesis protocols [21b,23] …”

Section: Figurementioning

confidence: 99%

Synthesis of Linear Enamides and Enecarbamates via Photoredox Acceptorless Dehydrogenation

et al. 2023

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In recent years, several methods for the direct desaturation of aliphatic compounds have been developed, facilitated by the unique combination of photoredox and transition‐metal catalysis. Hereby, alkenes with high functionalization potential can be prepared in a straightforward fashion. We adapted a previously reported system involving tetrabutylammonium decatungstate (TBADT) as hydrogen atom transfer (HAT) agent and a cobaloxime co‐catalyst for dihydrogen evolution for the dehydrogenative preparation of linear enamides and enecarbamates from saturated precursors. The substrate scope includes several natural products and drug derivatives. The reaction does not require noble metal catalysts, exhibits short reaction times compared to previous methods and is suitable for the late‐stage functionalization of drug derivatives.

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Section: Figurementioning

confidence: 99%

Synthesis of Linear Enamides and Enecarbamates via Photoredox Acceptorless Dehydrogenation

et al. 2023

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Synthesis of New Lansiumamide A/Alatamide (cis‐Isomer) Based Unnatural α‐Amino Acid Derivatives via the Suzuki‐Miyaura Cross Coupling as Key Step

et al. 2021

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We have developed a new synthetic method for the preparation of Lansiumamide-amino acid (1) as well as Alatamide (cisisomer)-amino acid (2) hybrids. The key step involves the Suzuki coupling reaction of N-((Z)-2-bromovinyl) cinnamamide with phenylboronic acid and (Z)-N-(2-iodovinyl)benzamide with 4-methoxy phenylboronic acid. The Suzuki coupling of N-((E)-2bromo-2-phenylvinyl) cinnamamide as well as (E)-N-(2-Iodo-2-(4-methoxyphenyl)vinyl)benzamide with 4-borono-pinacol ester of phenylalanine to give the Lansiumamide-phenylalanine and Alatamide (cis-isomer)-phenylalanine amino acid hybrids in good yields. This is the first synthesis of C-linked Lansiumamide A and Alatamide (cis-isomer)-amino acid conjugates where both the natural products are linked to amino acid through CÀ C bond.

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Design, synthesis and antifungal activities of novel cis-enamides via intermediate derivatization method

Xu¹,

Sun²,

Li³

et al. 2023

Advanced Agrochem

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Concise and Gram-Scale Total Synthesis of Lansiumamides A and B and Alatamide

Cited by 4 publications

References 23 publications

Synthesis of Linear Enamides and Enecarbamates via Photoredox Acceptorless Dehydrogenation

Synthesis of Linear Enamides and Enecarbamates via Photoredox Acceptorless Dehydrogenation

Synthesis of New Lansiumamide A/Alatamide (cis‐Isomer) Based Unnatural α‐Amino Acid Derivatives via the Suzuki‐Miyaura Cross Coupling as Key Step

Design, synthesis and antifungal activities of novel cis-enamides via intermediate derivatization method

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