A synthesis of a C1-C7 building block for the enantiomer of hennoxazole A utilizing a regioselective ring opening of a cyclic acetal

Heterocycles

Volumn 47, Issue 1, 1998, Pages 73-76

  Shioiri, Takayuki ^a   McFarlane, Nigel ^a   Hamada, Yasumasa ^b  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000628913     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-97-S(N)7     Document Type: Article

References (10)

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2. We selected the enantiomer of 1 as a synthetic target to investigate its possible biological activities. Synthesis of the enantiomer of 1 and determination of the absolute configuration were reported; see (a) P. Wipf and S. Lim, J. Am.Chem.Soc., 1995, 117, 558.
3. (b) P. Wipf and S. Lim, Chimia, 1996, 50, 157.
4. (a) A.G.M Barrett and J.T. Kohrt, Synlett, 1995, 415.
5. (b) Cheng, Z.; Hamada, Y.; Shioiri, T. Synlett, 1997, 109.
6. S. Saito, T. Hasegawa, M Inaba, R. Nishida, T. Fujii, S. Nomizu, and T. Moriwake, Chem. Lett., 1984, 1389.
7. A. Basha, M. Lipton, and S.M. Weinreb, Tetrahedron Lett., 1977, 4171.
8. The starting ester (5) was sometimes contaminated with methyl (S)-2,4-dihydroxybutyrate whose separation was difficult. However, after conversion to the Weinreb amides, the desired amide (7) could be purified by careful column chromatography on silica gel followed by recrystallization (ether/hexane).
9. (a) S.D. Rychnovsky, B. Roger, and G. Yang, J. Org. Chem., 1993, 58, 3511.
10. (b) Y. Hamada, F. Yokokawa, M. Kabeya, K. Hatano, Y. Kurono, and T. Shioiri, Tetrahedron, 1996, 52, 8297.