Triconoids A-D, Four Limonoids Possess Two Rearranged Carbon Skeletons from Trichilia connaroides

Org Lett. 2017 Apr 21;19(8):2182-2185. doi: 10.1021/acs.orglett.7b00873. Epub 2017 Apr 6.

Abstract

Four limonoids, triconoids A-C (1-3) possessing a new rearranged mexicanolide skeleton and triconoid D (4) furnishing a new rearranged 1,2-seco-phragmalin skeleton, were isolated from the Nepalese plant Trichilia connaroides. Two rearranged limonoid skeletons sharing an F ring of methyl 5-oxotetrahydrofuran-2-carboxylate were postulated to be formed biosynthetically via a very unique chemical cascade. Their structures were fully accomplished by spectroscopic data, single-crystal X-ray diffraction, and electrostatic circular dichroism analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biochemical Phenomena
  • Biosynthetic Pathways
  • Limonins / biosynthesis*
  • Limonins / chemistry
  • Meliaceae / metabolism*

Substances

  • Limonins