Asymmetric desymmetrization of meso-cyclopentitol using a C2-symmetric bis-sulfoxide: A synthesis of (−)-allosamizoline

Author:

Maezaki Naoyoshi,Sakamoto Atsunobu,Tanaka Tetsuaki,Iwata Chuzo

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference14 articles.

1. Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, S. J. Antibiot. 1987, 40, 296–300.

2. Somers, P. J. B.; Yao, R. C.; Doolin, L. E.; McGowan, M. J.; Fukuda, D. S.; Mynderse, J. S. J. Antibiot. 1987, 40, 1751–1756.

3. Koga, D.; Isogai, A.; Sakuda, S.; Matsumoto, S.; Suzuki, A.; Kimura, S.; Ide, A. Agric. Biol. Chem. 1987, 51, 471–476.

4. For synthesis of racemic allosamizoline, (a) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997–7000; (b) Trost, B. M.; Vranken, D. L. V. J. Am. Chem. Soc. 1993, 115, 444–458; (c) Trost, B. M.; Vranken, D. L. V. J. Am. Chem. Soc. 1990, 112, 1261–1263. For synthesis of (−)-allosamizoline from sugar: (d) Blattner, R.; Furneaux, R. H.; Kemmitt, T.; Tyler, P. C.; Ferrier, R. J.; Tiden, A.-K. J. Chem. Soc., Perkin Trans. 1 1994, 3411–3421; (e) Kitahara, T.; Suzuki, N.; Koseki, K.; Mori, K. Biosci. Biotech. Biochem. 1993, 57, 1906–1909; (f) Simpkins, N. S.; Stokes, S.; Whittle, A. J. J. Chem. Soc., Perkin Trans. 1 1992, 2471–2477; (g) Simpkins, N. S.; Stokes, S.; Whittle, A. J. Tetrahedron Lett. 1992, 33, 793–796; (h) Nakata, M.; Akazawa S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363–5366; (i) Takahishi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 38, 5123–5126. For synthesis of (−)-allosamizoline via enzymatic desymmetrization: (j) Shrader, W. D.; Imperiali, B. Tetrahedron Lett. 1996, 37, 599–602; (k) Griffith, D. A.; Danishefsky, S. J.; Samuel, J. J. Am. Chem. Soc. 1996, 118, 9526–8538; (l) Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1991, 113, 5863–5864.

5. Maezaki, N.; Sakamoto, A.; Soejima, M.; Sakamoto, I.; Li, Y.-X.; Tanaka, T.; Ohishi, H.; Sakaguchi, K.; Iwata, C. Tetrahedron: Asymmetry 1996, 7, 2787–2790 and references cited therein.

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