Abstract Oxidation of alcohols by methyl sulfide‐ N ‐chlorosuccinimide‐ triethylamine: 4‐ tert ‐butylcyclohexanone catalyst: 8.0 g. (0.060 mole) of N ‐chlorosuccinimide product: 4‐ tert ‐butylcyclohexanone byproduct: 4‐ tert ‐butylcyclohexylmethyl methylthiomethyl ether product: C6H5CHO

4-Thiazolidinones were synthesized and evaluated for their ability to inhibit the bacterial enzyme MurB. Selected 4-thiazolidinones displayed activity against the enzyme in vitro. This activity, coupled with the design principles of the thiazolidinones, supports the postulate that 4-thiazolidinones may be recognized as diphosphate mimics by a biological selector.

Cephalosporin derivatives containing a unique combination of lipophilic C-7 sidechains and polar C-3 thiopyridinium groups were synthesized and found to exhibit potent anti-MRSA activity in vitro and in vivo. The optimum C-7 sidechains utilized were 2,5-dichlorophenylthioacetamido and 2,6-dichloropyrid-4-ylthioacetamido. The C-3 thiopyridinium rings were substituted at nitrogen with amino acid and pyruvic acid groups that were designed to confer aqueous solubility as required for IV formulation. This paper describes the characteristics of these novel cephalosporins and highlights synthetic methods developed to allow their practical, large-scale syntheses.

Regiospecific synthesis of alkylated A ring of arotinoids has been achieved by using Me(3)Al-TMSOSO(2)CF(3) as a key reagent for conversion of carbonyl to a geminal dimethyl functionality.

A series of thymidine analogues substituted with alkoxy groups of the C-4 position of the furan ring were synthesized. Among these compounds, the methoxy analogue 9 was the most potent inhibitor of herpes simplex virus type 1 thymidine kinase.

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Regiospecific and highly Stereoselective electrophilic addition reactions to the furanoid glycal 10 have been used as key steps in the synthesis of ddA and d4T antiviral nucleosides.

A novel synthesis of 1-hydroxy-2-phosphonocyclobutenedione (4) is described.

Isosteric phosphonate analogues of acyclovir and ganciclovir monophosphates were synthesized. The new phosphonates exhibited good anti-herpes activity.

Novel phosphonate isosteres of acyclovir (ACV) and ganciclovir (DHPG) monophosphates (20 and 32) were found to be potent and selective antiherpesvirus agents. In the series of phosphonate analogues of ACV monophosphate, only the guanine analogue 20 exhibited activity against herpesviruses, similar to the structure-activity relationship observed for base modification of ACV analogues. The phosphonate isostere of ACV monophosphate (20) was more effective than ACV in the HSV-1 infected mouse model. The 3'-carba analogues of 9-[3-hydroxy-2-(phosphonomethoxy)propyl]purines/pyrimidines (adenine, HPMPA; guanine, HPMPG; cytosine, HPMPC) are devoid of antiherpesvirus activity. This result confirms that the beta-oxygen atom of the phosphonomethyl ether functionality in HPMP-purines/pyrimidines plays a critical role for activity against herpesviruses.

Phosphonate analogues of d4T and d4A monophosphates have been synthesized using stereocontrolled addition of dimethyl hydroxymethylphosphonate to furanoid glycals. The new phosphonates exhibited a potent activity against HIV.