Journal of Organic Chemistry p. 3428 - 3431 (1983)
Update date:2022-08-28
Topics:
Heathcock, Clayton H.
Jennings, Rex A.
von Geldern, Thomas W.
An approach to the synthesis of securinega alkaloids is reported.Reductive amination of ethyl-2-thienylacetoacetate (12) with methyl (S)-prolinate gives a mixture of diastereomeric amino diesters 6 and 13 in a ratio of 44:56.Dieckmann cyclization of the mixture followed by treatment of the product with acid affords the crystalline (+/-)-10 in 64percent yield.Separation of 6 and 13 prior to cyclization provides samples of the enantiomers (-)-10 and (+)-10, respectively.Attempts to open the thiophene ring of 10 were not successful.Treatment of (+/-)-10 with excess n-butyllithium and trimethylsilyl chloride results in a novel fragmentation, leading to the benzothiophene 18.
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