Sonogashira coupling of 2-iodo-2-cycloalkenones: Synthesis of (+)- and (-)-harveynone and (-)-tricholomenyn A

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1582-1583

  Miller, Michael W ^a,b   Johnson, Carl R ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; HARVEYNONE; TRICHOLOMENYN A; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030890077     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962295y     Document Type: Article

References (26)

1. Johnson, C. R.; Adams, J. P.; Bis, S. J.; DeJong, R. L.; Golebiowski, A.; Medich, J. R.; Penning, T. D.; Senanayake, C. H.; Steensma, D. H.; Van Zandt, M. C. Pure Appl. Chem. 1992, 64, 1115.
2. Enzymatic asymmetrization: Johnson, C. R.; Harikrishnan, L. S.; Golebiowski, A. Tetrahedron Lett. 1994, 35, 7735. Enzymatic resolution: Johnson, C. R.; Sakaguchi, H. Synlett 1992, 813. Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett. 1994, 35, 6975.
3. Enzymatic asymmetrization: Johnson, C. R.; Harikrishnan, L. S.; Golebiowski, A. Tetrahedron Lett. 1994, 35, 7735. Enzymatic resolution: Johnson, C. R.; Sakaguchi, H. Synlett 1992, 813. Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett. 1994, 35, 6975.
4. Enzymatic asymmetrization: Johnson, C. R.; Harikrishnan, L. S.; Golebiowski, A. Tetrahedron Lett. 1994, 35, 7735. Enzymatic resolution: Johnson, C. R.; Sakaguchi, H. Synlett 1992, 813. Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett. 1994, 35, 6975.
5. Suzuki coupling of a 2-iodo-2-cyclopentenone: (a) Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014. Stille coupling of 2-iodo-2-cycloalkenones: (b) Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919.
6. Suzuki coupling of a 2-iodo-2-cyclopentenone: (a) Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014. Stille coupling of 2-iodo-2-cycloalkenones: (b) Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919.
7. (a) Johnson, C. R.; Miller, M. W. J. Org. Chem. 1995, 60, 6674.
8. For a synthesis of (±)-bromoxone see: (b) Gautier, E. C. L.; Lewis, N. J.; McKillop, A.; Taylor, R. J. K. Tetrahedron Lett. 1994, 35, 8759.
9. (a) Nagata, T.; Ando, Y.; Hirota, A. Biosci. Biotech. Biochem. 1992, 56, 810.
10. (b) Kawazi, K.; Kobayashi, A.; Oe, K. JP 03 41,075, 1991; Chem. Abstr. 1991, 115, 181517k.
11. (b) Kawazi, K.; Kobayashi, A.; Oe, K. JP 03 41,075, 1991; Chem. Abstr. 1991, 115, 181517k.
12. (c) Kobayashi, A.; Ooe, K.; Yata, S.; Kawazu, K. Symposium of Papers, the 31st Symposium on the Chemistry of Natural Products, Nagoya, October 1989, pp 388-395.
13. (d) Garlaschelli, L.; Magistrali, E.; Vidari, G.; Zuffardi, O. Tetrahedron Lett. 1995, 36, 5633.
14. (a) Kamikubo, T.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1996, 1679.
15. (b) Graham, A. E.; McKerrecher, D.; Huw Davies, D.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 7445.
16. 7b examined a range of successful Sonagashira couplings with isomeric 3-iodo-2-cyclohexenones. The epoxyquinol products are very base sensitive, and in our hands it was found necessary to carefully remove all traces of amine promoters by extraction with cold aqueous 1 M HCl. Experimental details are not available in ref 7a,b; it is possible that their failures are attributable to workup conditions. The Sonogashira coupling reactions we examined proceeded faster with diisopropylamine than with triethylamine.
17. For one example of a successful Sonogashira coupling between a 2-bromo-2-cycloalkenone (2-bromo-2-cyclopentenone/THF/60°C) see: Buszek, K. R.; Jeong, Y. Synth. Commun. 1994, 24, 2461. For a recent review of the Sonogashira reaction see: Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. 1995, 27, 129.
18. For one example of a successful Sonogashira coupling between a 2-bromo-2-cycloalkenone (2-bromo-2-cyclopentenone/THF/60°C) see: Buszek, K. R.; Jeong, Y. Synth. Commun. 1994, 24, 2461. For a recent review of the Sonogashira reaction see: Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. 1995, 27, 129.
19. 7a Their synthesis of the enone (-)-11 is quite different from ours.
20. For α-iodination of enones see: Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917.
21. Pilcher, A. S.; Hill, D. K.; Shimshock, S. J.; Waltermire, R. E.; DeShong, P. J. Org. Chem. 1992, 57, 2492.
22. These are interesting analogues of the natural product (+)-bromoxone (ref 5). For a synthesis of (±)-13 see ref 7b.
23. Chiralcel OB: elution with i-PrOH/hexanes (15/85); 0.5 mL/min; 260 nm; 20 min (+)-13; 33 min (-)-13.
24. Chiralcel OB: elution with i-PrOH/hexanes (5/95); 0.5 mL/min; 260 nm; 39 min (-)-15 min; 47 min (+)-15.
25. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
26. Chiralcel OB: elution with i-PrOH/hexanes (5/95); 0.5 mL/min; 260 nm; 23 min (-)-22 min; 40 min (+)-22.