- COUMARINS OF MERRILLIA CALOXYLON
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Key Word Index--Merrillia caloxylon; Rutaceae; isoprenylcoumarins; murrangatin; mexoticin; (-)-phebalosin; sibiricin; 7-methoxy-8-(1',2'-dihydroxy-3'-methylbutyl)coumarin; merillin.Abstract--From the roots of Merrillia caloxylon the five isoprenylcoumarins (-)-sibiricin, (-)-phebalosin, (-)-murrangatin, (-)-mexoticin and merillin were isolated.
- Zakaria, Muhamad Bin,Saito, Isao,Matsuura, Teruo
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p. 657 - 659
(2007/10/02)
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- Studies on Rutaceae: Part VI - Reacrtions and Rearrangements of Coumarins
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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)
- Banerji, J.,Dhara, K. P.,Das, B.,Das, A. K.,Chatterjee, A.
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