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1.
ACS Omega ; 7(8): 7223-7228, 2022 Mar 01.
Article in English | MEDLINE | ID: mdl-35252712

ABSTRACT

A concise and practical synthesis has been developed to provide the 8-fluoro-5-hydroxy-3,4-diydrocarbostyril (8-FDC) fragment of OPC-167832 in 41% yield and in >99% purity over four steps from 3-amino-4-fluorophenol. The key feature of this process is the development of a telescoped one-pot synthesis of the quinolone via a chemoselective amidation/acid-induced cyclization that allows for simple product isolation without the need for column chromatography.

2.
J Org Chem ; 87(4): 2142-2153, 2022 02 18.
Article in English | MEDLINE | ID: mdl-34807603

ABSTRACT

Chiral γ-lactones are prevalent organic architectures found in a large array of natural products. In this work, we disclose the development of a modified catalytic system utilizing a commercially available Cu-phosphite catalyst for the diastereoselective reductive coupling of chiral allenamides and ketones to afford chiral γ-lactone precursors in 80:20 to 99:1 dr.


Subject(s)
Ketones , Catalysis , Stereoisomerism
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