Synthesis of New Lansiumamide A/Alatamide (cis‐Isomer) Based Unnatural α‐Amino Acid Derivatives via the Suzuki‐Miyaura Cross Coupling as Key Step. Issue 22 (10th June 2021)

• Record Type: Journal Article
• Authors: Sambaiah, M.; Thota, PradeepKumar; Kottawar, Shrinivas S.; Yennam, Satyanarayana; Shiva Kumar, K.; Behera, Manoranjan
• Is Part Of: ChemistrySelect. Volume 6:Issue 22(2021)
• Page Start: 5406
• Page End: 5410
• Publication Date: 2021-06-10
• Subjects: Alatamide (cis-isomer) -- Hybrid molecule -- Lansiumamide A -- Natural products -- Synthesis design -- Unnatural α-Amino Acid; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202101093
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: We have developed a new synthetic method for the preparation of Lansiumamide‐amino acid (1) as well as Alatamide ( cis ‐isomer)‐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)‐2‐bromo‐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 C−C bond. Abstract : A novel and efficient route for the preparation of Lansiumamide A‐amino acid as well as Alatamide (cis isomer)‐amino acid hybrids was developed. 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)‐2‐bromo‐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. The research revealed the first synthesis of C‐linked Lansiumamide A/Alatamide (cis‐isomer)‐Phenylalanine amino acid conjugates where both the natural products were linked to amino acid through C−C bond.