Total synthesis of (+)-1893B aimed at establishing its stereochemistry

Heterocycles

Volumn 67, Issue 1, 2006, Pages 123-128

  Yasui, Hiroyuki ^a   Hirai, Kunihiro ^a   Yamamoto, Shun ^a   Takao, Ken ichi ^a   Tadano, Kin ichi ^a  

^a KEIO UNIVERSITY   (Japan)

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Indexed keywords

EID: 33646893053     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-S(T)42     Document Type: Article

References (20)

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8. 3), IR] and gave satisfactory HRMS spectrum. Yields referred to homogeneous samples purified by chromatography on silica gel.
9. In a large-scale experiment, the diastereomer (7b) was isolated in some extent from the mixture by recrystallization with ethyl acetate.
10. Chataigner I., Lebreton J., Durand D., Guingant A., and Villiéras J. Tetrahedron Lett. 39 (1998) 1759
11. For a recent review of the assignment of absolute configuration by NMR spectrum, see:. Seco J.M., Quiñoá E., and Riguera R. Chem. Rev. 104 (2004) 17
12. According to the stereochemical outcome proposed by the Sharpless group, the anti epoxy alcohol was obtained preferentially. Rossiter B.E., Verhoeven T.R., and Sharpless K.B. Tetrahedron Lett. 49 (1979) 4733
13. Takano S., Kamikubo T., Sugihara T., Suzuki M., and Ogasawara K. Tetrahedron: Asymmetry 4 (1993) 201
14. We examined the ring-opening reactions of epoxy alcohols (10, 11a or 11b) by using nucleophiles such as acetic acid dianion, acetonitrile anion, or dimethyl malonate anion. None of these nucleophiles afforded the desired ring-opened products.
15. Compain P., Goré J., and Vatèle J.-M. Synlett 943 (1994)
16. Compain P., Goré J., and Vatèle J.-M. Tetrahedron 52 (1996) 10405
17. +) m/z 294.1467, found 294.1478.
18. +) m/z 292.1311, found 292.1316.
19. +) m/z 292.1311, found 292.1305.
20. 1H-NMR spectra of these diastereomers did not match that of the natural 1893B.