Implication and improvement of stereoselective methylenation of a chiral aldehyde related to total synthesis of the furaquinocins

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3755-3758

  Saito, Takeshi ^a   Suzuki, Takao ^a   Takeuchi, Kazuhiro ^a   Matsumoto, Takashi ^a   Suzuki, Keisuke ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; FURAQUINOCIN C; FURAQUINOCIN D;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030952703     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00746-6     Document Type: Article

References (23)

1. Funayama, S.; Ishibashi, M.; Anraku, Y.; Komiyama, K.; Omura, S. Tetrahedron Lett. 1989, 30, 7427; Ishibashi, M.; Funayama, S.; Anraku, Y.; Komiyama, K.; Omura, S. J. Antibiot. 1991, 44, 390.
2. Funayama, S.; Ishibashi, M.; Anraku, Y.; Komiyama, K.; Omura, S. Tetrahedron Lett. 1989, 30, 7427; Ishibashi, M.; Funayama, S.; Anraku, Y.; Komiyama, K.; Omura, S. J. Antibiot. 1991, 44, 390.
3. (a) Saito, T.; Morimoto, M.; Akiyama, C.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1995, 117, 10757.
4. (b) For the total synthesis of furaquinocin C, see: Smith, A. B., III; Sestelo, J. P.; Dormer, P. G. J. Am. Chem. Soc. 1995, 117, 10755.
5. (a) Corey, E. J.; Chaykovsky, M. J. J. Am. Chem. Soc. 1965, 87, 1353.
6. (b) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341.
7. (c) Johnson, C. R. In Comprehensive Organic Chemistry; Jones, N. D., Ed.; Pergamon: Oxford, U. K., 1979; Vol. 3, p 247.
8. (d) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424.
9. A full account of the total synthesis including the preparation of aldehyde 5 will appear in due course.
10. Stereochemical assignment of 6a and 6b relies on the correlation to the natural product, furaquinocin D, according to a similar route described in ref. 2a.
11. (a) Cohen, T.; Herman, G.; Chapman, T. M.; Kuhn, D. J. Am. Chem. Soc. 1974, 96, 5627.
12. (b) Taylor, E. C.; Chittenden, M. L.; Martin, S. F. Heterocycles 1973, 1, 59.
13. (a) Shanklin, J. R.; Johnson, C. R.; Ollinger, J.; Coates, R. M. J. Am. Chem. Soc. 1973, 95, 3429.
14. (b) Townsend, J. M.; Sharpless, K. B. Tetrahedron Lett. 1972, 3313.
15. 2 = 13.9 Hz, 1H), 2.46-2.48 (broad, 1H), 2.29 (s, 3H), 1.64 (d, J = 6.6 Hz, 3H), 1.56 (s, 3H).
16. -, then NaOH), and no crossover was observed for either case. See 7b.
17. Seeman, J. I. Chem. Rev. 1983, 83, 83.
18. Some reports have appeared recently that propose an oxathiethane, rather than a betaine, is more plausible as the intermediate of such reactions. See: Kawashima, T.; Ohno, F.; Okazaki, R.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 1996, 118, 12455.
19. (a) Johnson, C. R.; Haake, M.; Schroeck, C. W. J. Am. Chem. Soc. 1970, 92, 6594.
20. (b) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418.
21. Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
22. 4) and concentrated in vacuo. The residue was purified by PTLC (benzene/acetone = 9/1 for separating epoxides 6 from N,N-dimethylphenylsulfinamide) to afford a mixture of epoxide 6a and 6b (110 mg), which was subjected to HPLC analysis (Zorbax sil, 4.6 mm × 25 cm, hexane/THF = 8/2, flow rate 0.5 mL/s, 6a: 34.3 min, 6b: 51.4 min). The diastereomers were separated by PTLC (hexane/EtOAc = 3/2) to afford epoxide 6a (105 mg, 84%) and 6b (3.8 mg, 3%). 6a: Rf = 0.35 (hexane/acetone = 3/1). 6b: Rf = 0.39 (hexane/acetone = 3/1).
23. The reaction of (R)-8 was much slower, thereby giving many unidentified side products. In contrast, (S)-8 gave rise to a clean reaction.