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Synthesis of (.+-.)-endo- and (.+-.)-exo-brevicomin via ene reaction of the Pummerer rearrangement product derived from 4-chlorophenyl methyl sulfoxide.
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- ISHIBASHI HIROYUKI
- Kyoto Pharmaceutical University
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- UEHARA CHIAKI
- Kyoto Pharmaceutical University
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- KOMATSU HAJIME
- Kyoto Pharmaceutical University
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- IKEDA MASAZUMI
- Kyoto Pharmaceutical University
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Description
(±) -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).
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 35 (7), 2750-2754, 1987
The Pharmaceutical Society of Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282679141615872
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- NII Article ID
- 130003943881
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- ISSN
- 13475223
- 00092363
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- Text Lang
- en
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- Data Source
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- JaLC
- Crossref
- CiNii Articles
- OpenAIRE
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- Abstract License Flag
- Disallowed