Highly efficient method for coriolin synthesis

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 465-468

  Domon, Kei ^a   Masuya, Keiichi ^a   Tanino, Keiji ^a   Kuwajima, Isao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CORIOLIN; CYCLOPENTANONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0031012868     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02328-3     Document Type: Article

References (20)

1. Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I. Synlett 1996, 157-158. Similar methylenecyclopentane annulation could also be effected by using the substrate having a TMS-methyl group in place of the siloxy group of 2. Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946.
2. Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I. Synlett 1996, 157-158. Similar methylenecyclopentane annulation could also be effected by using the substrate having a TMS-methyl group in place of the siloxy group of 2. Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946.
3. Isolation and characterization of coriolin: a) Takeuchi, T.; Iinuma, H.; Iwanaga, J.; Takahashi, S.; Takita, T.; Umezawa, H. J. Antibiot. 1969, 22, 215-217.
4. b) Nakamura, H.; Takita, T.; Umezawa, H.; Kunishima, M.; Nakayama, Y. J. Antibiot. 1974, 27, 301-302 and references cited therein.
5. Total synthesis of coriolin: a) Mulzer, J. In Organic Synthesis Highlights, Mulzer, J.; Altenbach, H.-J.; Braun, M., Krohn, K., Reissig, H.-U., Eds.; VCH: Weinheim, 1991; pp 323-334 and references cited therein,
6. b) Funk, R. L.; Bolton, G. L.; Daggett, J. U.; Hansen, M. M.; Horcher, L. H. M. Tetrahedron 1985, 41, 3479-3495.
7. c)Magnus, P.; Exon, C.; Albaugh-Robertson, P. Tetrahedron 1985, 41, 5861-5869.
8. d)Mehta, G.; Murthy, A. N.; Reddy, D. S.; Reddy, A. V. J. Am. Chem. Soc. 1986, 108, 3443-3452.
9. e) Demuth, M.; Ritterskamp, P.; Weigt, E.; Schaffner, K. J. Am. Chem. Soc. 1986, 108, 4149-4154.
10. f) Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523-2525.
11. g) Hijfte, L. V.; Little, R. D.; Petersen, J. L.; Moeller, K. D. J. Org. Chem. 1987, 52, 4647-4661.
12. h) Weinges, K.; Braun, R.; Huber-Patz, U.; Irngartinger, H. Liebigs Ann. Chem. 1993, 1133-1140.
13. The spectral data of 7a were identical to those previously reported by Magnus and co-workers: see ref. 3c.
14. Gutierrez, C. G.; Summerhays, L. R. J. Org. Chem. 1984, 49, 5206-5213.
15. These conditions were originally reported for the protection of a carbonyl group as a dithio acetal rather than vinylsulfide: Ong, B. S.; Chan, T. H. Synth. Commun. 1977, 7, 283-286.
16. This transformation seems to proceed through the Michael addition of thiophenol to give the α-(methylthio)-β-(phenylthio)ketone which in turn leads to enone 13 by a nucleophilic attack of phenylthiolate anion on the methylthio group as shown below. For desulfurization of α-(alkylthio)ketones by the reactions with a thiolate anion, see: Oki, M.; Funakoshi, W.; Nakamura, A. Bull. Chem. Soc. Jpn. 1971, 44, 828-832.
17. (a) Grieco, P. A.; Nishizawa, M.; Oguri, T.; Burke, S. D.; Marinovic, N. J. Am. Chem. Soc. 1977, 99, 5773-5780.
18. (b) Demuynck, M.; De Clercq, P.; Vandewalle, M. J. Org. Chem. 1979, 44, 4863-4866.
19. The spectral data of 14 were identical to those previously reported: see ref. 3b and 3g.
20. Ito, T.; Tomiyoshi, N.; Nakamura, K.; Azuma, S.; Izawa, M.; Maruyama, F.; Yanagiya, M.; Shirahama, H.; Matsumoto, T. Tetrahedron 1984, 40, 241-255.