Efficient synthesis of a carbocyclic core moiety with the stereochemistry of the C-1027 chromophore

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5135-5138

  Sato, Itaru ^a   Akahori, Yuri ^a   Iida, Kyo Ichiro ^a   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALDEHYDE; KEDARCIDIN;

ARTICLE; CHROMATOPHORE; CYCLIZATION; DIASTEREOISOMER; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0030586209     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01036-2     Document Type: Article

References (27)

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2. 1. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2633-2636; Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M. ; Otani, T. Tetrahedron Lett. 1993, 34, 2637-2640; Yoshida, K.; Minami, Y.; Otani, T.; Tada, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 5253-5256.
3. 1. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2633-2636; Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M. ; Otani, T. Tetrahedron Lett. 1993, 34, 2637-2640; Yoshida, K.; Minami, Y.; Otani, T.; Tada, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 5253-5256.
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5. 3. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875-8876. For reviews of related syntheses, see: Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416; Hirama, M. Synthesis and Chemistry of Neocarzinostatin Analogs. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol 2; Lukacs, G. Ed.; Springer-Verlag: Berlin, 1993; pp. 293-329; Hirama M. J. Syn. Org. Chem. Jpn. 1994, 52, 980-991.
6. 3. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875-8876. For reviews of related syntheses, see: Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416; Hirama, M. Synthesis and Chemistry of Neocarzinostatin Analogs. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol 2; Lukacs, G. Ed.; Springer-Verlag: Berlin, 1993; pp. 293-329; Hirama M. J. Syn. Org. Chem. Jpn. 1994, 52, 980-991.
7. 3. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875-8876. For reviews of related syntheses, see: Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416; Hirama, M. Synthesis and Chemistry of Neocarzinostatin Analogs. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol 2; Lukacs, G. Ed.; Springer-Verlag: Berlin, 1993; pp. 293-329; Hirama M. J. Syn. Org. Chem. Jpn. 1994, 52, 980-991.
8. 3. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875-8876. For reviews of related syntheses, see: Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416; Hirama, M. Synthesis and Chemistry of Neocarzinostatin Analogs. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol 2; Lukacs, G. Ed.; Springer-Verlag: Berlin, 1993; pp. 293-329; Hirama M. J. Syn. Org. Chem. Jpn. 1994, 52, 980-991.
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14. 6. For related addition reactions, see: Nakatani, K.; Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron, 1992, 48, 633-650; Chattopadhyay, A.; Mamdapur, V. R. J. Org. Chem. 1995, 60, 585-587; Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron, 1990, 46, 265-276. (equation presented)
15. 3.
16. 2: C, 65.17; H, 8.75. Found: C, 64.98; H, 8.50.
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20. 12
21. 12
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25. 12), 160.0.
26. 16. Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694-695. For ten-membered ring formation, see: Nishikawa, T.; Isobe, M.; Goto, T. Synlett, 1991, 393-395.
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