Spirotrichilins A and B: Two Rearranged Spirocyclic Limonoids from Trichilia connaroides

Org Lett. 2016 Apr 15;18(8):1924-7. doi: 10.1021/acs.orglett.6b00738. Epub 2016 Apr 7.

Abstract

Spirotrichilins A (1) and B (2), two novel limonoids with an unprecedented spiro[cyclopenta[b]furan-2,1'-cyclopentan] ring system in A/B/C rings, were isolated from the fruits of trichilia connaroides. Their planar structures and absolute configurations were established based on 1D-, 2D-NMR data, electronic circular dichroism (ECD) exciton chirality method and time-dependent density functional theory (TDDFT)/ECD calculation. A benzilic acid-like rearrangement in ring A was proposed as the key step in the plausible biogenetic pathway of 1 and 2.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biochemical Phenomena
  • Circular Dichroism
  • Fruit
  • Limonins / chemical synthesis*
  • Limonins / chemistry
  • Magnetic Resonance Spectroscopy
  • Meliaceae / chemistry*
  • Molecular Structure
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry

Substances

  • Limonins
  • Spiro Compounds
  • spirotrichilin A
  • spirotrichilin B