Stereoselective synthesis of 4-aryl-2-(benzyloxy)carbonyl-3-hydroxy tetrahydrofurans from aryl epoxides

Author:

Angle Steven R.,White Stephen L.

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference8 articles.

1. For recent examples and leading references see: (a) Hartung, J.; Schmidt, P. Synlett 2000, 367–370. (b) Yoda, H.; Shimojo, T.; Takabe, K. Synlett 1999, 1969–1971. (c) Gruttadauria, M.; Lo Meo P.; Noto, R. Tetrahedron 1999, 55, 14097–14110. (d) Craig, D.; Ikin, N. J.; Mathews, N.; Smith, A. M. Tetrahedron 1999, 55, 13471–13494. (e) Zhang, H.; Seepersaud, M.; Seepersaud, S.; Mootoo, D. R. J. Org. Chem. 1998, 63, 2049–2052. (f) Marshall, J. A.; Jiang, H. Tetrahedron Lett. 1998, 39, 1493–1496. (g) Craig, D.; King, N. P.; Shaw, A. N. Tetrahedron Lett. 1997, 38, 8599–8602. (d) Petasis, N. A.; Lu, S.-P. J. Am. Chem. Soc. 1995, 117, 6394–6395. (h) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4187–4188.

2. (a) Angle, S. R.; Bernier, D. S.; Chann, K.; Jones, D. E.; Kim, M.; Neitzel, M. L.; White, S. L. Tetrahedron Lett. 1998, 39, 8195–8198. (b) Angle, S. R.; Bernier, D. S.; El-Said, N. A.; Jones, D. E.; Shaw, S. Z. Tetrahedron Lett. 1998, 39, 3919–3922.

3. Stereoselective synthesis of substituted tetrahydrofurans via Lewis acid promoted reaction of .beta.-benzyloxyaldehydes and ethyl diazoacetate.

4. (a) Yamamoto, H.; Maruoka, K.; Ooi, T. J. Am. Chem. Soc. 1989, 111, 6431–6432. (b) Yamamoto, H.; Maruoka, K.; Ooi, T.; Nagahara, S. Tetrahedron 1991, 47, 6983–6998.

5. (a) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1993, 115, 12208–12209. (b) Jung, M. E.; Marquez, R. Tetrahedron Lett. 1999, 40, 3129–3132. (c) Jung, M. E.; Lee, W. S.; Sun, D. Org. Lett. 1999, 2, 307–309.

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