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1.
J Org Chem ; 85(13): 8339-8351, 2020 07 02.
Article in English | MEDLINE | ID: mdl-32462862

ABSTRACT

An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high yields. By adapting this methodology, a convergent synthesis of a complex target of HCV NS3/4a protease inhibitor BI 201420 was accomplished.


Subject(s)
Hepatitis C , Viral Nonstructural Proteins , Antiviral Agents , Ethers , Hepacivirus , Humans , Protease Inhibitors/pharmacology , Sulfones
2.
J Org Chem ; 82(10): 5456-5460, 2017 05 19.
Article in English | MEDLINE | ID: mdl-28459568

ABSTRACT

An efficient and practical synthesis of enantiomerically pure P-chiral dihydrobenzooxaphosphole (BOP) core 1 is developed that is amenable to large scale preparation of the related ligand series. The unique epimerization of the P-chiral center of the undesired (R,R)-diastereomeric phosphine oxide 19 through chlorination followed by crystallization makes this chemical resolution method achieve 65% yield of desired (R,S)-diastereomer 12.

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