Synthetic study of the kedarcidin chromophore: Efficient construction of the aryl alkyl ether linkage

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8707-8710

  Kawata, Shinji ^a   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Cesium and compounds; Diynes; Etherification; Phenolics

Indexed keywords

ANTINEOPLASTIC AGENT; CESIUM; CYCLOPENTADIENE DERIVATIVE; EPOXIDE; KEDARICIDIN; PHENOL DERIVATIVE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHROMATOPHORE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; STEREOCHEMISTRY;

EID: 0032547988     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01914-5     Document Type: Article

References (18)

1. [1] Leet JE, Schroeder DR, Langley DR, Colson KL, Huang S, Klohr S. E, Lee MS, Golik J, Hofstead SJ, Doyle TW, Maison JA. J. Am. Chem. Soc. 1993; 115: 8432-8433.
2. [2] Kawata S, Ashizawa S, Hirama M. J. Am. Chem. Soc. 1997; 119:12012-12013.
3. [3] Reddy RS, Iguchi S, Kobayashi S, Hirama M. Tetrahedron Lett. 1996; 37: 9335-9336.
4. [4] Iida K, Hirama M. J. Am. Chem. Soc. 1994; 116: 10310-10311.
5. [5] For synthetic studes, see: (a) Iida K, Hirama M. J. Am. Chem. Soc. 1995; 117: 8875-8876.; Kawata S, Yoshimura F, Irie J, Ehara H, Hirama M. Synlett, 1997; 250-252.
6. [5] For synthetic studes, see: (a) Iida K, Hirama M. J. Am. Chem. Soc. 1995; 117: 8875-8876.; Kawata S, Yoshimura F, Irie J, Ehara H, Hirama M. Synlett, 1997; 250-252.
7. (b) Myers AG, Horiguchi Y. Tetrahedron Lett. 1997; 38: 4363-4366.
8. (c) Homyák M, Pelyvás IF. Sztaricskai FJ. Tetrahedron Lett. 1993; 34: 4087-4090.; Vuljanic T, Kihlberg J, Somfai P. Tetrahedron Lett. 1994; 37: 6937-6940.; Toshima K, Yoshida T, Mukaiyama S, Tatsuta K. Carbohydrate Research 1991; 222: 173-188.
9. (c) Homyák M, Pelyvás IF. Sztaricskai FJ. Tetrahedron Lett. 1993; 34: 4087-4090.; Vuljanic T, Kihlberg J, Somfai P. Tetrahedron Lett. 1994; 37: 6937-6940.; Toshima K, Yoshida T, Mukaiyama S, Tatsuta K. Carbohydrate Research 1991; 222: 173-188.
10. (c) Homyák M, Pelyvás IF. Sztaricskai FJ. Tetrahedron Lett. 1993; 34: 4087-4090.; Vuljanic T, Kihlberg J, Somfai P. Tetrahedron Lett. 1994; 37: 6937-6940.; Toshima K, Yoshida T, Mukaiyama S, Tatsuta K. Carbohydrate Research 1991; 222: 173-188.
11. [6] For condensation of phenols and epoxides, see: (a) David M, Sauleau J, Sauleau A. Can. J. Chem. 1985; 63: 2449-2454.
12. (b) Riego J, Costa A, Saa JM. Chem. Lett. 1986; 27: 1565-1566.
13. (c) Schultz AG, Lucci RD, Fu WY, Berger MH, Erhardt J, Hagmann WK. J. Am. Chem. Soc. 1978; 100: 2150-2162.
14. (d) Jung ME, Starkey LS. Tetrahedron Lett. 1995; 36: 7363-7366.
15. (e) Akita H, Umezawa I, Takano M, Ohyama C, Matsukura H, Oishi T. Chem. Pharm. Bull. 1993; 41: 55-63.
16. (f) Klunder JM, Ko YS, Sharpless KB. J. Org. Chem. 1986; 51: 3710-3712.
17. [7] (a) Nambu Y, Endo T. Tetrahedron Lett. 1990; 31: 1723-1726.
18. (b) For related CsF mediated alkylations, see: Kitaori K, Furukawa Y, Yoshimoto H, Otera J. Tetrahedeon Lett. 1998; 39: 3173-3176, and references cited therein.