Synthesis and olfactory evaluation of optically active β-alkyl substituted γ-lactones and whiskey lactone analogues

Kawasaki, Masashi; Kato, Daiki; Okada, Takuya; Morita, Yuko; Tanaka, Yasuo; Toyooka, Naoki

doi:10.1016/j.tet.2020.130984

Cited by 3 publications

(1 citation statement)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…γ-Lactones and γ-lactams are common structural motifs in bioactive compounds, including molecules with anticancer, antiviral, or antibiotic activities, but also in a number of fragrances. − While they have raised significant interest from the synthetic community, the stereodivergent synthesis of highly substituted γ-lactones and γ-lactams still constitutes a formidable challenge. − …”

Section: Introductionmentioning

confidence: 99%

Stereodivergent Synthesis of 1,4-Dicarbonyl Compounds through Sulfonium Rearrangement: Mechanistic Investigation, Stereocontrolled Access to γ-Lactones and γ-Lactams, and Total Synthesis of Paraconic Acids

G.-Simonian,

Spieß,

Riomet

et al. 2024

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Although simple γ-lactones and γ-lactams have received considerable attention from the synthetic community, particularly due to their relevance in biological and medicinal contexts, stereoselective synthetic approaches to more densely substituted derivatives remain scarce. The in-depth study presented herein, showcasing a straightforward method for the stereocontrolled synthesis of γ-lactones and γ-lactams, builds on and considerably expands the stereodivergent synthesis of 1,4-dicarbonyl compounds by a ynamide/vinyl sulfoxide coupling. A full mechanistic and computational study of the rearrangement was conducted, uncovering the role of all of the reaction components and providing a rationale for stereoselection. The broad applicability of the developed tools to streamlining synthesis is demonstrated by concise enantioselective total syntheses of (+)-nephrosteranic acid, (+)-rocellaric acid, and (+)-nephromopsinic acid.

show abstract