Palladium-catalyzed coupling of alkenyl iodides with ethynyl oxiranes: Synthesis of epoxy enediyne core intermediates related to neocarzinostatin chromophore

Tetrahedron Letters

Volumn 37, Issue 52, 1996, Pages 9335-9336

  Reddy, Ravinder S ^a   Iguchi, Satoru ^a   Kobayashi, Shoji ^a   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; ZINOSTATIN CHROMOPHORE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030599681     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)82957-7     Document Type: Article

References (18)

1. 1. Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120-4122; Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851-9853; Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310-10311.
2. 1. Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120-4122; Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851-9853; Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310-10311.
3. 1. Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120-4122; Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851-9853; Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310-10311.
4. 2. For related approaches, see the reviews: (a) 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;
5. (b) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416;
6. (c) Lhermitte, H.; Grierson, D. S.; Contemp. Org. Synth. 1996, 3, 93-124.
7. 3. Sato, I.; Akahori, Y.; Iida, K.; Hirama, M. Tetrahedron Lett. 1996, 37, 5135-5138.
8. 4. Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiot. 1965, 18, 68-76; Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331-334.
9. 4. Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiot. 1965, 18, 68-76; Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331-334.
10. 5. Hirama, M. J. Syn. Org. Chem. Jpn. (in English) 1994, 52, 980-991.
11. 6. Ishii, M.; Ando, T.; Kajiura, T.; Kameyama, T.; Nihei, Y. Jpn. Kokai Tokkyo Koho JP 07291955; Chem. Abst. 1996, 124, 115564h.
12. 6. Ishii, M.; Ando, T.; Kajiura, T.; Kameyama, T.; Nihei, Y. Jpn. Kokai Tokkyo Koho JP 07291955; Chem. Abst. 1996, 124, 115564h.
13. 7. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 50, 4467-4470;
14. (b) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138-2152 and references cited therein.
15. 8. Pale, P.; Bertus, P. Tetrahedron Lett. 1996, 37, 2019-2022.
16. 3 10. Synthesized from D-mannitol and the details will be reported separately.
17. 13C-NMR, and HRMS.
18. 12 Ethynyl oxirane 5a was added dropwise to the reaction mixture: the slow addition of 5a increased the yield of 1.