Abstract
α,11α-Epoxyfernane possessing a cis-fused B/C rings derived from fern-9(11)-ene isolated from Drynaria quercifolia on treatment with BF3.Et2O in nonpolar solvent like benzene afforded fern-7(8),9(11)-diene as the sole product. On the other hand, 9α,11α-epoxyisoarborinyl acetate having a trans-fused B/C rings gave earlier, besides only traces of the corresponding 7(8),9(11)- diene and 11α-hydroxy-8(9)-ene, a unique rearranged product, in which ring B has expanded to a 7-membered ring containing a keto carbonyl function at C-9 with concomitant contraction of ring C to a 5-membered ring by migration of 8,9-bond to C-11. The observed differences in the products profile in the two reactions were rationalized in terms of the different stereochemistry of the B/C ring juncture of the two oxirane derivatives.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
