Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/95125
Title: Synthesis of lucidones
Authors: Lee, H.-H. 
Que, Y.-T.
Ng, S.
Issue Date: 1985
Source: Lee, H.-H.,Que, Y.-T.,Ng, S. (1985). Synthesis of lucidones. Journal of the Chemical Society, Perkin Transactions 1 : 453-455. ScholarBank@NUS Repository.
Abstract: Reaction of 2-cinnamoyl-3-hydroxy-5-methoxy-1,4-benzoquinone (10) with acetic anhydride-dimethyl sulphoxide yielded (E)-4-(cinnamoylmethylene)-2- methoxybut-2-en-4-olide (4). Assignment of configuration of the exocyclic double bond in (4) is based on comparison of 1H n.m.r. shift data and 3J(C-3,5-H) value with those of 4-ylidenebutenolides (11)-(13). In the presence of sodium methoxide, (4) undergoes ready rearrangement affording lucidone (1a) and hence methyl-lucidone (1b).
Source Title: Journal of the Chemical Society, Perkin Transactions 1
URI: http://scholarbank.nus.edu.sg/handle/10635/95125
ISSN: 14727781
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