Preparation of Alkyl-Substituted Indoles in the Benzene Portion. Part 9.1) Synthesis of (1aS,8bS)-1 -tert-Butyloxycarbonyl-8-formy 1-1,1 a,2,8b-tetrahydroazirino[2‘,3’: 3,4]pyrrolo[ 1,2-a]indole. Model Study for the Enantiospecific Synthesis of Aziridinomitosenes

Chemical and Pharmaceutical Bulletin

Volumn 41, Issue 5, 1993, Pages 854-860

  Utsunomiya, Iwao ^a   Sato, Tomohiro ^b   Fuji, Masahiro ^b   Natsume, Mitsutaka ^b  

^a Kawasaki   (Japan)

^b SHIONOGI AND CO LTD   (Japan)

Author keywords

1H NMR configuration determination; aziridinomitosene model; chiral aldehyde a indole substitution; chiral synthesis; Keywords tetrahydroazirinopyrroloindole; X ray crystallographic analysis

Indexed keywords

1 TERT BUTYLOXYCARBONYL 8 FORMYL1,1A,2,8B TETRAHYDROAZIRINO[2',3':3,4]PYRROLO[1,2 A]INDOLE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0027214104     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.41.854     Document Type: Article

References (18)

1. Utsunomiya, H. Muratake, and M. Natsume, Chem. Pharm. Bull., 40, 2358 (1992).
2. M. Fuji, H. Muratake, and M. Natsume, Chem. Pharm. Bull., 40, 2344 (1992).
3. Isolation and biological activity: S. Kiyoto, T. Shibata, M. Yamashita, T. Komori, M. Okuhara, H. Terano, M. Kohsaka, H. Aoki, and H. Imanaka, J. Antibiot., 40, 594 (1987).
4. I. Uchida, S. Takase, H. Kayakiri, S. Kiyoto, M. Hashimoto, T. Tada, S. Koda, and Y. Morimoto, J. Am. Chem. Soc., 109, 4108 (1987).
5. T. Fukuyama, L. Xu, and S. Goto, J. Am. Chem. Soc., 114, 383 (1992).
6. T. Fukuyama and S. Goto, Tetrahedron Lett., 30, 6491 (1989)
7. K. F. McClure and S. J. Danishefsky, J. Org. Chem., 56, 850 (1991)
8. R. M. Williams and S. R. Rajski, Tetrahedron Lett., 33, 2929 (1992).
9. R. J. Sundberg and H. F. Russell, J. Org. Chem., 38, 3324 (1973).
10. M. G. Saulnier and G. W. Gribble, J. Org. Chem, 47, 757 (1982).
11. K. Nakajima, T. Tanaka, K. Morita, and K. Okawa, Pept. Chem., 15, 127 (1978)
12. K. Nakajima Abstr., 93, 168584n (1980)].
13. P. Garner and J. M. Park, J. Org. Chem., 52, 2361 (1987).
14. K. C. Nicolaou, R. A. Daines, J. Uenishi, W. S. Li, D. P. Papahatjis, and T. K. Chakraborty, J. Am. Chem. Soc., 109, 2205 (1987).
15. M. Cherest, H. Felkin, and N. Prudent, Tetrahedron Lett., 1968, 2199
16. N. T. Anh, Top. Curr. Chem., 88, 145 (1980)
17. R. S. Coleman and A. J. Carpenter, Tetrahedron Lett., 33, 1697 (1992)
18. K. Nakajima, F. Takai, T. Tanaka, and K. Okawa, Bull. Chem. Soc. Jpn., 51, 1577 (1978).