Bicunningines A and B, two new dimeric diterpenes from Cunninghamia lanceolata

Org Lett. 2012 Jan 20;14(2):460-3. doi: 10.1021/ol202915r. Epub 2011 Dec 27.

Abstract

Two unprecedented dimeric diterpenoids, with a 2,3-dihydrofuran ring fusing an abietane and a 4,5-seco-abietane diterpene, were isolated from Cunninghamia lanceolata. Their structures were elucidated by spectroscopic measurements, and their absolute configurations were determined by quantum chemical TDDFT ECD calculations, chemical transformations, and Mosher's method. The Mosher method carried out with MPA and MTPA esters of the sterically hindered sec-hydroxyl group gave contradictory results, while MPA afforded the correct absolute configuration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cunninghamia / chemistry*
  • Dimerization
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Models, Molecular
  • Molecular Conformation

Substances

  • Diterpenes
  • bicunningine A
  • bicunningine B