Details

Autor(en) / Beteiligte

• Villagómez-Guzmán, Ana K.
• Hernández-Padilla, Laura
• Rodríguez-García, Gabriela
• Cortés-García, Carlos J.
• Campos-García, Jesús
• del Río, Rosa E.
• Thomassigny, Christine
• Gómez-Hurtado, Mario A.

Titel

High stereoselective semisynthesis of kauroxane and beyeroxane compounds

Ist Teil von

• Journal of molecular structure, 2024-06, Vol.1306, p.137904, Article 137904

Ort / Verlag

Elsevier B.V

Erscheinungsjahr

2024

Quelle

Elsevier ScienceDirect Journals

Beschreibungen/Notizen

• •Kaurenoic or beyerenoic acid as substrates to explore stereoselective Prins reaction.•Quirality from natural diterpenes directly influences the Prins-cyclization process.•Highly stereoselective Prins-cyclization in diterpene skeletons favors fused oxane ring.•The mechanism of Prins-cyclization is proposed and supported by computational means.•Cytotoxic potential of kauroxane and beyeroxane is explored in vitro assays. A semisynthetic strategy to access novel kauroxane or beyeroxane compounds from ent‑kauranal or ent‑beyerenal, respectively, is described. A Prins cyclization was used as a key step reaction to synthesize diterpene-tetrahydropyran hybrid compounds with high stereoselectivity by using 3-buten-1-ol as oxane precursor and indium trichloride as the Lewis acid catalyst. The absolute configurations of new compounds were determined by mechanistic means and supported with DFT calculations, as well as considering the stereoselectivity behavior associated with the chiral purity of diterpenes and their conformational restrictions. The structures were elucidated by their physical and spectroscopic data. Finally, the antiproliferative activity of the target molecules was done, being moderately bioactive. [Display omitted]