Details

Autor(en) / Beteiligte

• Omar, Ashraf M.
• Sun, Sijia
• Kim, Min Jo
• Tawila, Ahmed M
• Dibwe, Dya Fita
• Phrutivorapongkul, Ampai
• Toyooka, Naoki
• Awale, Suresh

Titel

Fragranol A: A new class of spiro-triflavanoid hybrid with an unprecedented carbon skeleton from Anneslea fragrans

Ist Teil von

• Tetrahedron letters, 2020-07, Vol.61 (29), p.152099, Article 152099

Ort / Verlag

Elsevier Ltd

Erscheinungsjahr

2020

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• [Display omitted] •A new class of “spiro-triflavanoid” hybrid with an unprecedented carbon skeleton.•Fragranol A (1) with six chiral centers, including two spiro-chiral carbons.•Absolute configuration determination by experimental and ECD calculations.•Spatial anisotropic effects by syn- or anti-group effect the NMR chemical shift. Phytochemical investigation of Anneslea fragrans twigs resulted in the discovery of fragranol A (1), a new class of structurally challenging and sterically hindered “spiro-triflavanoid” type compound possessing an unprecedented carbon skeleton. Fragranol A (1) consists of 45 carbons having six chiral carbons, including two spiro-chiral centers. Structural elucidation of 1 was achieved by HRFABMS, 1D and 2D NMR, analysis of spatial anisotropic effects, and quantum ECD calculations. A plausible biogenetic pathway of 1 is also proposed.