59056-65-4Relevant academic research and scientific papers
A novel one-pot synthesis of 8-acetoxymethylisolongifolene and 8-acetoxymethylcycloisolongifolene from longifolene
Nayak, U. R.,Deodhar, V. B.,Dalavoy, V. S.
, p. 912 - 914 (2007/10/02)
Boron trifluoride etherate-induced dual catalysis of the rearrangement of longifolene (1) to isolongifolene (2) and a concomitant formaldehyde addition to 2 in acetic acid medium is achieved in a one-pot reaction to give a mixture of 8-acetoxymethylisolongifolene (3) and 8-acetoxymethylcycloisolongifolene (4), not separable by chromatography.On hydrolysis of the acetate mixture followed by Jones' oxidation of the resultant alcohols 6 and 7, only the former generates the aldehyde 8 while the latter yields the acid 9.Lithium aluminium hydride reduction of 8/9 back to the parent alcohols 6/7 followed by acetylation enables preparation of the pure acetates 3/4 by a chemical method.
