Improved synthesis of diquinones

Synlett

Volumn , Issue 5, 2009, Pages 0813-0817

  Love, Brian E ^a   Bonner Stewart, Jeffrey ^b   Forrest, Lori A ^b  

^a EAST CAROLINA UNIVERSITY   (United States)

^b PhytoMyco Research Corporation   (United States)

Author keywords

CAN; Dimerizations; Oxidations; Quinones; Reaction protocols

Indexed keywords

EID: 62449124772     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087937     Document Type: Article

References (27)

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7. (b) Note: cyclization of the corresponding diquinone to yield popolohuanone E has not yet been reported, owing to difficulties in preparation of the requisite diquinone 1. See: Munday, R. H.; Denton, R. M.; Anderson, J. C. J. Org. Chem. 2008, 73, 8033.
8. (a) Jacob, P. III.; Callery, P. S.; Shulgin, A. T.; Castagnoli, N. Jr. J. Org. Chem. 1976, 41, 3627.
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16. 11 reports a 75% yield of 6a and does not report a yield for 7a.
17. Initially this was done unintentionally.
18. Hayashi, N.; Yoshikawa, T.; Ohnuma, T.; Higuchi, H.; Sako, K.; Uekusa, H. Org. Lett. 2007, 9, 5417.
19. Applicability of the method to hydrophobic substrates becomes particularly relevant if the method is to be applied to the synthesis of popolohuanone E and related compounds, since the presumed precursor to popolohuanone E contains a large alicyclic side chain (in addition to an additional hydroxyl group; Scheme 1).
20. 13C NMR spectra were obtained on crude products. These spectra indicated that compounds prepared by 'inverse' addition were typically devoid of any significant impurities. Products purified by recrystallization were used to obtain melting point data.
21. -1.
22. 6): δ = 6.95 (s, 2 H), 6.81 (s, 2 H), 4.76 (t, J = 5.4 Hz, 2 H), 3.59 (dt, J = 5.4, 6.0 Hz, 4 H), 2.55 (t, J = 6.0 Hz, 4 H).
23. Dimethyl acetals of 2,5-dimethoxybenzaldehyde and 2′,5′- dimethoxyacetophenone both returned only the unprotected carbonyl compounds under these reaction conditions.
24. Ring nitration of electron-rich benzenes using CAN supported on silica has previously been reported. See: Grenier, J.-L.; Catteau, J.-P.; Cotelle, P. Synth. Commun. 1999, 29, 1201.
25. 2O (2:1) per mmol of substrate. Both employed CAN solutions that were approximately 1 M.
26. 2O. See: Dinctürk, S.; Ridd, J. H. J. Chem. Soc., Perkin Trans. 2 1982, 965.
27. Hewgill, F. R.; Hewitt, D. G. J. Chem. Soc. C 1967, 723.