Fused cyclic ether formations from bromo-diepoxides by AgOTf-promoted successive ring expansion reactions

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6173-6176

  Hayashi, Nobuyuki ^a   Fujiwara, Kenshu ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE;

ARTICLE; CONFORMATIONAL TRANSITION; CYCLIZATION; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0030593593     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01340-8     Document Type: Article

References (12)

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6. 2. a) N. Hayashi, K. Fujiwara, and A. Murai, Chem. Lett. 1996, 341-342;
7. for ring expansion, see: b) E. Alvarez, M. T. Díaz, R. Pérez, J. L. Ravelo, A. Regueiro, J. A. Vera, D. Zurita, and J. D. Martín, J. Org. Chem. 1994, 59, 2848-2876.
8. c) T. Nakata, G. Schmid, B. Vranesic, M. Okigawa, T. Smith-Palmer, and Y. Kishi, J. Am. Chem. Soc. 1978, 100, 2933-2935.
9. d) T. Nakata, S. Nomura, and H. Matsukura, Tetrahedron Lett. 1996, 37, 213-216.
10. e) T. Nakata, S. Nomura, H. Matsukura, and M. Morimoto, Tetrahedron Lett. 1996, 37, 217-220.
11. 3. Diepoxides (1a and 1b), prepared as a 1:1 mixture of two diastereomers in 12 steps and a 31% overall yield from the 4-pentyn-1-ol, were separated by HPLC. The structures of 1a and 1b were determined by NMR analyses (H-H coupling constants and NOEs) of the acetates of 9a and 9b, respectively.
12. ++H), 559.1798.