Synthesis of (±)-endo- and (±)-exo-Brevicomin via Ene Reaction of the Pummerer Rearrangement Product Derived from 4-ChIorophenyl Methyl Sulfoxide(Organic,Chemical)
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概要
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(±)-endo- (4) and (±)-exo-Brevicomin (5) were synthesized by employing the ene-type reaction of 4-chlorophenylthiomethyl trifluoroacetate (2) as the key step. The ene product 7 was converted, via two steps, into the ketosulfone 9, whose epoxidation followed by acid hydrolysis afforded the cyclic acetal as a mixture, 12a and 12b (89:11). Recrystallization of the mixture followed by desulfurization yielded (±)-endo-brevicomin (4). On the other hand, successive treatment of 9 with osmium tetroxide, hydrochloric acid, and Raney nickel afforded a mixture of (±)-exo- (5) and (±)-endo-brevicomin (4) (89:11).
- 公益社団法人日本薬学会の論文
- 1987-07-25
著者
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池田 正澄
Kyoto Pharmaceutical University
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小松 一
Kyoto Pharmaceutical University
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石橋 弘之
Kyoto Pharmaceutical University
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上原 千秋
Kyoto Pharmaceutical University
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