Concise asymmetric synthesis of a model compound, (4S,5S,6S)-6-(2,2-dimethoxy)ethyl-4,5-epoxy-6-hydroxy-2-cyclohexenone, for the cyclohexenone core of scyphostatin

Author:

Fujioka Hiromichi,Kotoku Naoyuki,Sawama Yoshinari,Nagatomi Yasushi,Kita Yasuyuki

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference11 articles.

1. For the structure determination of scyphostatin including the absolute configurations of the cyclohexanone unit and biological activity, see: Tanaka, M.; Nara, F.; Suzuki, K.; Hosoya, T.; Ogita. T. J. Am. Chem. Soc. 1997, 119, 7871–7872; Nara, F.; Tanaka, M.; Hosoya, T.; Suzuki-Konagai, K.; Ogita, T. J. Antibiot. 1999, 52, 525; Nara, F.; Tanaka, M.; Masuda-Inoue, S.; Yamamoto, Y.; Doi-Yoshioka, H.; Suzuki-Konagai, K.; Kumakura, S.; Ogita, T. J. Antibiot. 1999, 52, 531.For the determination of the absolute configurations of the side chain, see: Saito, S.; Tanaka, N.; Fujimoto, K.; Kogen, H. Org. Lett. 2000, 2, 505–506. Fpr an alternative study on the synthesis and configuration of scyphostatin side chain, see: Hoye, T. R.; Tennakoon, M. A. Org. Lett. 2000, 2, 1481–1483.

2. The sphingomyelin pathway in tumor necrosis factor and interleukin-1 signaling

3. For a synthetic study for cyclohexenone segment in optically active form, see: (a) Gurjar, M. K.; Hotha, S. Heterocycles 2000, 53, 1885–1889; (b) Izuhara, T.; Katoh, T. Tetrahedron Lett. 2000, 41, 7651–7655; (c) Izuhara, T.; Katoh, T. Org. Lett. 2001, 3, 1653–1656; (d) Izuhara, T.; Yokota, Y.; Inoue, M.; Katoh, T. Heterocycles 2002, 56, 553–560. For a synthetic study for cyclohexenone segment in non-optically active form, see: (e) Runcie, K. A.; Taylor, R. J. K. Org. Lett. 2001, 3, 3237–3239.

4. For intramolecular haloetherification of ene acetals prepared from chiral non-racemic hydrobenzoin and achiral ene aldehyde, see: (a) Fujioka, H.; Kitagawa, H.; Matsunaga, N.; Nagatomi, Y.; Kita, Y. Tetrahedron Lett. 1996, 37, 2245–2248; (b) Fujioka, H.; Kitagawa, H.; Nagatomi, Y.; Kita, Y. J. Org. Chem. 1996, 61, 7309–7315.

5. Cyclohexa-2,5-dienylethanal diethylacetal was prepared from benzoic acid in a four-steps sequence according to the literature procedure (Scholz, D.; Schmidt, U. Chem. Ber. 1974, 107, 2295–2298). Transacetalization of cyclohexa-2,5-dienylethanal diethylacetal with (R,R)-hydrobenzoin afforded 2. The details of these reactions will be published elsewhere.

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