Acid-catalyzed O-allylation of β-hydroxy-α-amino acids: an entry into conformationally constrained dipeptide surrogates

• Published in: Bioorganic & medicinal chemistry letters 1992-06, Vol.2 (6), p.579-582
• Main Authors: Burkholder, Timothy P., Le, Tieu-Binh, Giroux, Eugene L., Flynn, Gary A.
• Format: Article
• Language: English
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(01)81201-4

O-Allylation using allyl trichloroimidate 5 was found to be an effective method for the introduction of an acetaldehyde equivalent onto the hydroxyl group of β-hydroxy-α-amino acid derivatives. Rigid oxygen containing tricyclic anti-phenylalanylleucine mimic 1 was efficiently synthesized using this method. This mimetic was further elaborated to provide 7c, a potent inhibitor of angiotensin-1 converting enzyme (ACE). O-Allylation using allyl trichloroimidate 5 was found to be an effective method for the introduction of an acetaldehyde equivalent onto the hydroxyl group of β-hydroxy-α-amino acid derivatives. Rigid oxygen containing tricyclic anti-phenylalanyl-leucine mimic 1 was efficiently synthesized using this method. This mimetic was further elaborated to provide 7c, a potent inhibitor of angiotensin-1 converting enzyme (ACE).