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

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

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.

Original languageEnglish
Article number152099
JournalTetrahedron Letters
Volume61
Issue number29
DOIs
StatePublished - 2020/07/16

Keywords

  • Absolute configuration
  • Anisotropic shielding
  • Anneslea fragrans
  • Spiro-flavanoid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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