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1.
ACS Comb Sci ; 22(1): 1-5, 2020 01 13.
Article in English | MEDLINE | ID: mdl-31860283

ABSTRACT

An efficient approach to the parallel synthesis of benzimidazoles from anilines is described. Library approaches to vary the N1 and C2 vectors of benzimidazoles are well established; however, C4-C7 variation has traditionally relied on 1,2-dianiline building blocks, providing limited chemical space coverage. We have developed an amidine formation/oxidative cyclization sequence that enables anilines as a diversity set for benzimidazole C4-C7 SAR generation in parallel format. The amidine annulation was achieved using PIDA or Cu-mediated oxidation to access both N-H and N-alkyl benzimidazoles. This library protocol has now been utilized for analog production in four medicinal chemistry projects. Additionally, the synthesis of aza-benzimidazoles from aminopyridines was achieved via an analogous sequence.


Subject(s)
Benzimidazoles/chemical synthesis , Aniline Compounds/chemistry , Benzimidazoles/chemistry , Chemistry, Pharmaceutical/methods , Cyclization , Oxidation-Reduction , Small Molecule Libraries/chemical synthesis , Structure-Activity Relationship
2.
Org Lett ; 17(5): 1102-5, 2015 Mar 06.
Article in English | MEDLINE | ID: mdl-25674920

ABSTRACT

The structure of the capsular polysaccharide (CPS) of serotype Ia group B Streptococcus (GBS) has been characterized for years, but its repeating unit, which is a challenging pentasaccharide with a branch and a difficult α-sialic acid linkage, has not been synthesized yet. In this report, an effective synthesis was developed for the serotype Ia GBS CPS repeating unit, which had a reactive functionality linked to its main-chain reducing end to enable further elaboration, such as coupling with carrier proteins. The target molecule was accomplished by a convergent [2 + 3] glycosylation strategy employing a sialo-disaccharide as donor and a branched trisaccharide as acceptor. The strategy was designed to suit the synthesis of oligomers of the repeating unit.


Subject(s)
Polysaccharides, Bacterial/chemical synthesis , Streptococcus/chemistry , Glycosylation , Molecular Structure , N-Acetylneuraminic Acid/chemistry , Polysaccharides, Bacterial/chemistry , Streptococcal Infections
3.
Org Lett ; 16(7): 1956-9, 2014 Apr 04.
Article in English | MEDLINE | ID: mdl-24673388

ABSTRACT

An enantiocontrolled synthesis pathway has been developed to provide formation of tricyclic amine 7, representing the ABC ring system of the complex alkaloid daphnicyclidin A (1). Our efforts describe preparation of the Z-hexahydro-(1H)-azocine 29 and cyclization to construct the novel 4-azabicyclo[5.3.2]dodecane 31. Transannular reductive amination following the deprotection of 31 gave the desired tertiary amine 7.


Subject(s)
Alkaloids/chemical synthesis , Alkaloids/chemistry , Cyclization , Molecular Structure , Saxifragaceae/chemistry , Stereoisomerism
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