Enantioselective Syntheses of (+)- and (−)-Blastmycinolactol

Author:

Jacobi Peter A.,Herradura Prudencio

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference32 articles.

1. Antimycin isolation: (a) Leben, C.; Keitt, G.W. Phytopath. 1948, 38, 899. (b) Watanabe, K.; Tanaka, T.; Fukuhara, K.; Miyairi, N.; Yonehara, H.; Umezawa, H. J. Antibiot. 1957, 10A, 39.

2. Blastmycinone isolation and structure: (a) Tener, G.M.; van Tamelen, E.E.; Strong, F.M. J. Am. Chem. Soc. 1953, 75, 3623. (b) Yonehara, H.; Takeuchi, S. J. Antibiot. 1958, 11A, 122, 254. (c) van Tamelen, E.E.; Strong, F.M.; Quarck, U.C. J. Am. Chem. Soc. 1959, 81, 750. (d) van Tamelen, E.E.; Dickie, J.P.; Loomans, M.E.; Dewey, R.S.; Strong, F.M. J. Am. Chem. Soc. 1961, 83, 1639. (e) Birch, A.J.; Cameron, D.W.; Harada, Y.; Rickards, R.W. J. Chem. Soc. 1961, 889. (f) Kinoshita, M.; Aburaki, S.; Wada, M.; Umezawa, S. Bull. Chem. Soc. Jpn. 1973, 46, 1279,

3. Blastmycinone synthesis: (a) de Azevedo, M.B.M.; Greene, A.E. J. Org. Chem. 1995, 60, 4940. (b) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201. (c) Nishide, K.; Aramata, A.; Kamanaka, T.; Inoue, T.; Node, M. Tetrahedron 1994, 50, 8337. (d) Mukai, C.; Kataoka, O.; Hanaoka, M. J. Org. Chem. 1993, 58, 2946, and references cited therein. Blastmycinolactol synthesis: (e) Mikami, K.; Terada, M.; Nakai, T. J. Chem. Soc., Chem. Commun. 1993, 343. (f) See also Ref. 2f and 3a–d.

4. (a) Li. W.; Nihira, T.; Sakuda, S.; Nishida, T.; Yamada, Y. J. Ferment. Bioeng. 1992, 74, 214. Synthesis:

5. (b) Nishida, T.; Nihira, T.; Yamada, Y. Tetrahedron 1991, 47, 6623. See also Ref. 3b.

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