Synthesis of A‑Type Proanthocyanidins and Their Analogues: A Comprehensive Review

• Published in: Journal of agricultural and food chemistry Vol. 68; no. 31; pp. 8104 - 8118
• Main Authors: Alejo-Armijo, Alfonso, Salido, Sofía, Altarejos, Joaquı́n
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 05.08.2020
• Subjects: chalcone; Chemistry Techniques, Synthetic - methods; developmental stages; flavanols; food chemistry; Lewis acids; Molecular Structure; proanthocyanidins; Proanthocyanidins - chemical synthesis; Proanthocyanidins - chemistry; analogues to A-type PACs; condensed tannins; A-type proanthocyanidins (PACs); 2,8-dioxabicyclo[3.3.1]nonane skeleton; organic synthesis
• ISSN: 0021-8561; 1520-5118; 1520-5118
• DOI: 10.1021/acs.jafc.0c03380

Proanthocyanidins (PACs) are oligomers or polymers composed of units of flavanols. A-type PACs are a subclass of PACs characterized by the presence of at least a double linkage between two consecutive monomers of flavanol. These A-type PACs are found in some fruits and spices and possess potential health benefits as a result of their interesting biological activities, and consequently, their isolation and synthesis have given rise to great interest in the past. This review summarizes the synthetic efforts made to obtain both naturally occurring A-type PACs and their structurally simplified analogues. Most of the synthetic protocols reported involve the addition of a π-nucleophilic molecule over a molecule with two electrophilic carbons, such as a chalcone, a flavylium salt, or a flavanol derivative, among others. Synthesis of A-type PACs remains an issue at a very early stage of development compared to that of PACs with single linkages between monomers (B-type PACs), but the advances that are taking place in the last few years point to a significant development of the subject in the near future.