Enantioselective synthesis of A 3,5,5-trialkylated tetronic acid derivative

Heterocycles

Volumn 77, Issue 1, 2009, Pages 167-172

  Takao, Ken ichi ^a   Kojima, Yuki ^a   Miyashita, Tomo ^a   Yashiro, Kentaro ^a   Yamada, Tatsuya ^a   Tadano, Kin ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Dieckmann Condensation; Guttiferae; Perforatumone; Sharpless Asymmetic Epoxidation

Indexed keywords

EID: 65549083754     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(F)11     Document Type: Article

References (23)

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15. 3), and IR] and gave satisfactory HRMS (EI). Yields refer to homogeneous samples purified by chromatography on silica gel.
16. R = 29.9 min for benzoate of 6, 25.8 min for the enantiomer).
17. Treatment of 6 with vinylmagnesium bromide and copper iodide produced a significant amount of the corresponding bromohydrin, formed by the ring opening with a bromide ion. The desired hotnoallylic alcohol was rather insufficiently obtained. This issue was avoided by the protection of the primary hydroxy group.
18. +) m/z 338.1729, found 338.1731.
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23. +) m/z 394.2355, found 394.2350.