79320-80-2Relevant academic research and scientific papers
Cyclisation Reactions: Part VII - Boron Trifluoride Catalysed Cyclisation of Di-epoxide Derived from (6E)-9-m-Methoxyphenyl-2,6-dimethylnona-2,6-diene: Formation of A-Homo-4a-oxa-13-methoxypodocarpa-8,11,13-trien-3β-ol
Nasipuri, Dhanonjoy,Samaddar, Ashis K.
, p. 261 - 263 (2007/10/02)
The di-epoxide derived from (6E)-9-m-methoxyphenylnona-2,6-diene on cyclisation with boron trifluoride etherate affords a stereoisomeric mixture of A-homo-4a-oxa-13-methoxypodocarpa-8,11,13-trien-3β-ol.The structure of the product has been confirmed by PMR and mass spectra.Apparently, the central epoxide oxygen makes a nucleophilic attack on the terminal epoxide ring (complexed with boron trifluoride) forming a seven-membered oxa-ring and generating a cationic centre which subsequently undergoes ring-closure with the aromatic ring in a non-stereospecific way.
