A short enantioselective synthesis of (−)-chloramphenicol and (+)-thiamphenicol using tethered aminohydroxylation

Synthesis, Characterization, and Antimicrobial Studies of Novel Benzodipyran Analog of Chloramphenicol

“…The present study has shown that for both antibacterial and antifungal activities of series of coumarin derivatives (2)(3)(4)(5)(6)(7), involving four strains of bacteria and fungi, in four concentrations (100, 50, 25, and 10 mg/mL, respectively), it is observed that the benzodipyran analog of chloramphenicol 7 was most active against Gram-positive bacteria, S.a, and the fungal strains R.b and P even at 10 mg/mL and showed moderate activity for other bacterial and fungal organisms when compared with their precursors (2)(3)(4)(5)(6). In this paper, we have established the detail structureantimicrobial activity relationship of 2-7 with standard chloramphenicol (drug sample).…”

“…In view of the various biological properties associated with coumarins in general and chloramphenicol in particular, it was thought to be of interest to incorporate the active 2-dichloroacetamidopropandiol side chain of chloramphenicol in to the C-9 position of benzodipyran, and the benzodipyran analog of chloramphenicol is synthesized (Scheme 1). A detail structure-antimicrobial activity relationship study was developed to deduce possible antimetabolite-metabolite relationships between the derivatives of coumarin (2)(3)(4)(5)(6), benzodipyran analog of chloramphenicol (7), and chloramphenicol (drug) in this paper.…”

Stereoselective Synthesis of (−)‐Chloramphenicol, (+)‐Thiamphenicol and (+)‐Sphinganine via Chiral Tricyclic Iminolactone

“…[17] Similarly, the synthesis of B (Scheme 2) started with the aldol reaction of tricyclic iminolactone 1a with p-methylsulfonylbenzaldehyde in the presence of 1.3 equiv. Our previous work demonstrated that when enolate of 1a reacted with aromatic aldehydes (e.g.…”

“…[9][10][11] For example, the β-galactosyl ceramide, plakoside A, isolated from the marine sponge Plakortis simplex, was found to be a noncytotoxic immunosuppressant. [17][18][19][20][21][22][23][24][25][26][27] As part of our continuous work on the stereoselective synthesis of α-amino acid using chiral tricyclic iminolactone which is derived from natural (1R)-(＋)-camphor, [28][29][30][31][32][33][34][35][36][37] we successfully developed a concise and effective methodology to synthesize optically pure β-hydroxy-α-amino acid. [14,15] However, it is not an easy task to synthesize glycosphingolipids for extensive research purpose.…”

The Influence of Exocyclic Stereochemistry on the Tethered Aminohydroxylation Reaction

“…By using these principles, the TA reaction has been used as a key step in the stereoselective synthesis of a range of biologically active compounds and natural products that uses aspects of both cyclic [11][12][13][14][15][16] and acyclic stereocontrol. [17][18][19][20] Attention was then turned to the possibility of inducing diastereoselectivity by using a stereocenter that is located outside (exo) of the heterocycle formed in the reaction (see 3!4). We report herein the results of this investigation, which reveal for the first time that a range of chiral allylic ethers can be oxidized into the corresponding amino alcohols in high yields and with up to 20:1 anti/syn stereoselectivity.…”