Flavonoids are plant‐derived dietary components with a substantial impact on human health. Research has expanded massively since it began in the 1930s, and the complex pathways involved in bioavailability of flavonoids in the human body are now well understood. In recent years, it has been appreciated that the gut microbiome plays a major role in flavonoid action, but much progress still needs to be made in this area. Since the first publications on the health effects of flavonoids, their action is understood to protect against various stresses, but the mechanism of action has evolved from the now debunked simple direct antioxidant hypothesis into an understanding of the complex effects on molecular targets and enzymes in specific cell types. This review traces the development of the field over the past 8 decades, and indicates the current state of the art, and how it was reached. Future recommendations based on this historical analysis are (a) to focus on key areas of flavonoid action, (b) to perform human intervention studies focusing on bioavailability and protective effects, and (c) to carry out cellular in vitro experiments using appropriate cells together with the chemical form of the flavonoid found at the site of action; this could be the native form of compounds found in the food for studies on digestion and the intestine, the conjugated metabolites found in the blood after absorption in the small intestine for studies on cells, or the chemical forms found in the blood and tissues after catabolism by the gut microbiota.

https://onlinelibrary.wiley.com/doi/pdf/10.1111/1541-4337.12351

The Bioavailability, Transport, and Bioactivity of Dietary Flavonoids: A Review from a Historical Perspective.

Phenyl-γ-valerolactones and phenylvaleric acids, the main colonic metabolites of flavan-3-ols: synthesis, analysis, bioavailability, and bioactivity

Absorption, metabolism, distribution and excretion of (−)-epicatechin: A review of recent findings

Construction of 2-Substituted-3-Functionalized Benzofurans via Intramolecular Heck Coupling: Application to Enantioselective Total Synthesis of Daphnodorin B

Recommending flavanols and procyanidins for cardiovascular health: revisited

The first enantioselective syntheses of sulfur flavan-3-ol analogues 1–8 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom. The key steps were: (a) Pd(0) catalyzed introduction of –S t-butyl group, (b) Sharpless enantioselective dihydroxylation of the alkene, (c) acid catalyzed ring closure to produce the thiopyran ring, and (d) removal of benzyl groups using N,N-dimethylaniline and AlCl3. The compounds were isolated in high chemical and optical purity.

Enantioselctive syntheses of sulfur analogues of flavan-3-Ols.

Disclosed are novel compounds represented by Structural Formula II, IX or XXVIII: R1, R2, and R22 are independently an aliphatic group, a substituted aliphatic group, an aromatic group or a substituted aromatic group. R2 is —NR4R5 or —N+≡C−. Alternatively, R1, and R2, taken together with the methine group to which they are bonded, are a moiety represented by the following structural formula: R3 is —NH2, —OH, —OC(O)H or —OR9. R5, R6 and R7 are independently —H or an amine protecting group. R8 is —H, —OH or —OR8. R9 is an alcohol protecting group. Also disclosed are methods of preparing these compounds.

Amino acid derivatives and methods of making the same

A process for the preparation of prostaglandin compounds having the formula (I): wherein A is selected from the group consisting of C1–C6 alkyl groups; C7–C16 aralkyl groups wherein an aryl portion thereof is unsubstituted or substituted with one to three substituents selected from the group consisting of C1–C6 alkyl groups, halo and CF3; and (CH2)nOR′ wherein n is an integer from 1 to 3 and R′ represents a C6–C10 aryl group which is unsubstituted or substituted with one to three substituents selected from the group consisting of C1–C6 alkyl groups, halo and CF3; B is selected from OR″ and NHR″ wherein R″ is C1–C6 alkyl groups; and

Protected diols for prostaglandin synthesis

Disclosed are novel compounds represented by structural Formula (XX), (XXI) or (XXII); R1, R21 and R22 are independently an aliphatic group, a substituted aliphatic group, an aromatic group or a substituted aromatic group. R2 and R12 are independently -NR4R5 or -N?+ C-. R?3 is -H or an alcohol protecting group. R4 and R5 are independently -H or an amine protecting group. R11 is a side chain of a naturally occurring amino acid or a protected side chain of a naturally occurring amino acid. R1 and R2, and R11 and R12, taken together with the methine group to which they are bonded, can form a moiety represented by structural Formula (XXIII). R6 is -H or an amine protecting group. R7 is -H, -OH or -OR8. R8 is an alcohol protecting group. Also disclosed are methods of preparing these compounds.

Building blocks derived from 1,2-aminoalcohols

A process for the preparation of prostaglandin compounds having the formula (I): 
wherein A is selected from the group consisting of C 1 –C 6 alkyl groups; C 7 –C 16 aralkyl groups wherein an aryl portion thereof is unsubstituted or substituted with one to three substituents selected from the group consisting of C 1 –C 6 alkyl groups, halo and CF 3 ; and (CH 2 ) n OR′ wherein n is an integer from 1 to 3 and R′ represents a C 6 –C 10 aryl group which is unsubstituted or substituted with one to three substituents selected from the group consisting of C 1 –C 6 alkyl groups, halo and CF 3 ; B is selected from OR″ and NHR″ wherein R″ is C 1 –C 6 alkyl groups; and

Jurjus Jurayj

Papers

Enantioselctive syntheses of sulfur analogues of flavan-3-Ols.

Amino acid derivatives and methods of making the same

Protected diols for prostaglandin synthesis

Building blocks derived from 1,2-aminoalcohols

Protected and unprotected triols for prostaglandin synthesis