88948-23-6Relevant articles and documents
Alloisolongifolene: A Unique Acid-catalysed Isomer of Longifolene
Shitole, H. R.,Vyas, P.,Nayak, U. R.
, p. 702 - 706 (2007/10/02)
A catalyst-specific rearrangement of longifolene (1) to a new tricyclic isomer, alloisolongifolene (10) is described.The structure (10) for alloisolongifolene has been derived by an X-ray crystal structure analysis of the p-nitrobenzoate (9) prepared from the primary alcohol (8) resulting from the hydroboration of the 10.Hydrolysis of the ester resulting from the Baeyer-Villiger oxidation of the methyl ketone (14) derived from the periodate-permanganate oxidation of 10 gives the trisnor C12-tertiary alcohol (16).Chromic acid oxidation of 10 generates the same carbon--cleaved ketone (14) and alloisolongifolic acid (15) derived from a terminal oxidation of the olefin.