Viswanatha, Venkatappa and Rao, GS Krishna (1974) Studies in terpenoids. Part XXXI. Synthesis of pyrocurzerenone, a furosesquiterpenoid from Curcuma zedoaria. In: Perkin Transactions 1 (4). pp. 450-453.
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7-Acetonyloxy-5-methyl--tetralone (Vc) was cyclodehydrated to 7,8-dihydro-1,5-dimethylnaphtho[2,1-b]furan-9(6H)-one (VIa), the structure of which was established by an independent synthesis from methyl 4-(4-acetonyloxy-2-methylphenyl)butyrate (IXd). Similarly, 7-acetonyloxy-2,5-dimethyl--tetralone (Vf), synthesized via 4-(5-isopropyl-4-methoxy-2-methylphenyl)-2-methylbutyric acid (XIIb) and 7-methoxy-2,5-dimethyl--tetralone (Vd), was cyclodehydrated to 7,8-dihydro-1,5,8-trimethylnaphtho[2,1-b]furan-9(6H)-one (VIb), which on reduction and dehydration furnished pyrocurzerenone (6,7-dihydro-1,5,8-trimethylnaphtho[2,1-b]furan)(I). The deisopropylation and cyclodehydration of (XIIb) to (Vd) were effected in one step by treatment with polyphosphoric acid.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to Royal Society of Chemistry.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||22 Dec 2009 09:03|
|Last Modified:||19 Sep 2010 05:50|
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