115071-67-5Relevant academic research and scientific papers
Studies on Rutaceae: Part VI - Reacrtions and Rearrangements of Coumarins
Banerji, J.,Dhara, K. P.,Das, B.,Das, A. K.,Chatterjee, A.
, p. 21 - 25 (2007/10/02)
Interesting reactions and rearrangements of isoprenoid systems have been observed in naturally occuring compounds like 6-(3',4'-epoxy-3'-methyl-γ-butyrolactonyl)-7-methoxycoumarin (micromelumin) (1), 7-methoxy-8-(1',2'-epoxy-3'-methylbut-3'-enyl)coumarin (phebalosin) (2), 7-methoxy-8-(2'-hydroxy-3'-methylbut-3'-enyl)coumarin (auraptenol) (3) and 7-methoxy-8-(3'-methylbut-2'-enyl)coumarin (osthol) (4).These reactions/rearrangements have led to the synthesis of coumarins already isolated from nature.Micromelumin (1) with pyridinium chloride affords the naturally occuring angelical (5), 6-(3'-methyl-3'-chloro-4'-hydroxy-γ-butyrolactonyl)- 7-methoxycoumarin (6b), 7-methoxycoumarinyl-6-tetronic acid derivative (7) and 6-(1'-carboxy-2'-methyl-3',4'-dihydroxybutenyl)-7-methoxycoumarin (8).Phebalosin (2) has been used for the hemisynthesis of the two naturally occuring diastereoisomeric coumarins minumicrolin (9) and murrangatin (10).Osthol (4) and auraptenol (3) have been used for the synthesis of the naturally occuring arnottinin (14)
STUDIES ON RUTACEANE: PART VII - AN INTERESTING REARRANGEMENT OF THE RARE EPOXYCOUMARIN. MICROMELUMIN, TO THE LINEAR FURANOCOUMARIN, PSORALEN
Banerji, Julie,Das, Anup K.,Das, Biswanath
, p. 2871 - 2875 (2007/10/02)
Boron terifluoride etherate treatment of 7-methoxy-6-γ-butyrolactone-3'-methyl-3',4'-epoxycoumarin (micromelumin), a consistuent of Micromelum pubescens Blume (Rutaceae), afforded an interesting rearranged product, psoralen, in addition to 7-methoxycoumarinyl-6-tetronic acid derivative.
