59056-64-3Relevant 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.
8-Methyleneisolongifolane/8-Methylisolongifolene: Synthesis and Reactions of Their Epoxides with Boron Trifluoride Etherate
Goudgaon, N. M.,Reddy, R. Thimma,Nayak, U. R.
, p. 487 - 492 (2007/10/02)
Wittig olefination of 7αH-8-oxoisolongifolane (2) generates 7βH-8-methyleneisolongifolane (4), which on exposure to BF3*OEt2 smoothly rearranges to the tetrasubstituted 8-methylisolongifolene (5).Action of BF3*OEt2 on the two epoxides 6/7 derived from 4/5 results in the unusual formation of the primary alcohol (9)/olefin (10) involving a concomitant cyclopropanation in both the cases.The β-stereochemistry for the hydroxymethyl group at C-8 in 9 has been derived by a direct coorelation of 9 with the known C15-cyclopropyl secondary alcohol (17).The cyclopropyl olefin (10) has been synthesised by dehydration of the tertiary alcohol (24) (resulting from the methyllithium reaction of the ketone 23 derived from 17).Epoxidation-isomerization of 10 generates the tetracyclic ketone (25).
