Synthesis of 1′-Homologated-3′-Modified Adenosine Derivatives through Asymmetric Intramolecular S N 2′ Alkylation Using an Evans Chiral Auxiliary

Key Points

• This research aims to synthesize novel 1'-homologated-3'-modified adenosine derivatives as potential PPARγ modulators.
• Developed synthesis using Evans oxazolidinone-based methodology.
• Carried out asymmetric intramolecular S_N2' alkylation.
• Used density functional theory calculations to analyze cis-selectivity and transition states.
• Successfully synthesized 1'-homologated-3'-modified adenosine derivatives.
• Achieved high stereoselectivity for cis-tetrahydrofuran through specific interactions.
• Density functional theory confirmed stabilizing noncovalent interactions influencing product formation.

Abstract