1634
Vol. 56, No. 11
ed. by Patai S., Rappoport Z., John Wiley & Sons, Chichester, 1988.
2) “Naturally Occurring Quinones IV Recent Advances,” ed. by Thom- 30) Marcotullio M. C., Epifano F., Curini M., Trends Org. Chem., 10, 21—
son R. H., Blackie Academic & Professional, London, 1997. 34 (2003).
3) Dudfield P. J., “Comprehensive Organic Synthesis,” Vol. 7, ed. by 31) Typical reaction procedure: Compound 1 (0.050 mmol) was added to a
29) Yakura T., Konishi T., Synlett, 2007, 765—768 (2007).
Trost B. M., Fleming I., Elsevier, Oxford, 1991, pp. 345—356.
4) Review: Gallagher P. T., Contemp. Org. Synth., 3, 433—446 (1996).
5) Review: Akai S., Kita Y., Org. Prep. Proced. Int., 30, 603—629
(1998).
6) Review: Owton W. M., J. Chem. Soc., Perkin Trans. 1, 1999, 2409—
2420 (1999).
7) Nojima S., Schal C., Webster F. X., Santangelo R. G., Roelofs W. L.,
Science, 307, 1104—1106 (2005).
8) Nicolaou K. C., Li H., Nold A. L., Pappo D., Lenzen A., J. Am. Chem.
Soc., 129, 10356—10357 (2007).
9) Tietze L. F., Singidi R. R., Gericke K. M., Chem. Eur. J., 13, 9939—
9947 (2007).
10) Tohma H., Morioka H., Harayama Y., Hashizume M., Kita Y., Tetrahe-
dron Lett., 42, 6899—6902 (2001).
11) “Hypervalent Iodine in Organic Synthesis,” ed. by Varvoglis A., Acad-
emic Press, San Diego, 1997.
12) Review: Wirth T., Hirt U. H., Synthesis, 1999, 1271—1287 (1999).
13) Review: Wirth T., Angew. Chem. Int. Ed., 40, 2812—2814 (2001).
14) Review: Zhdankin V. V., Stang P. J., Chem. Rev., 102, 2523—2584
(2002).
15) Review: Wirth T., Angew. Chem. Int. Ed., 44, 3656—3665 (2005).
16) Review: Dohi T., Kita Y., Kagaku, 61, 68—69 (2006).
17) Review: Richardson R. D., Wirth T., Angew. Chem. Int. Ed., 45,
4402—4404 (2006).
18) Dohi T., Maruyama A., Yoshimura M., Morimoto K., Tohma H., Kita
Y., Angew. Chem. Int. Ed., 44, 6193—6196 (2005).
19) Ochiai M., Takeuchi Y., Katayama T., Sueda T., Miyamoto K., J. Am.
Chem. Soc., 127, 12244—12245 (2005).
20) Yamamoto Y., Togo H., Synlett, 2006, 798—800 (2006).
21) Dohi T., Maruyama A., Minamitsuji Y., Takenaga N., Kita Y., Chem.
Commun., 2007, 1224—1226 (2007).
22) Richardson R. D., Page T. K., Altermann S., Paradine S. M., French A.
N., Wirth T., Synlett, 2007, 538—542 (2007).
23) Akiike J., Yamamoto Y., Togo H., Synlett, 2007, 2168—2172 (2007).
24) Yamamoto Y., Kawano Y., Toy P. H., Togo H., Tetrahedron, 63, 4680—
4687 (2007).
25) Richardson R. D., Desaize M., Wirth T., Chem. Eur. J., 13, 6745—
6754 (2007).
26) Moroda A., Togo H., Synthesis, 2008, 1257—1261 (2008).
27) Thottumkara A. P., Bowsher M. S., Vinod T. K., Org. Lett., 7, 2933—
2936 (2005).
solution of 2 (1.0 mmol) in CF3CH2OH–H2O (1 : 2, 10 ml), followed by
Oxone® (4 mmol) at room temperature, the resulting mixture was
stirred at the same temperature. After 2 was consumed completely, as
indicated by TLC, the mixture was diluted with ethyl acetate and
washed with water. The organic layer was then washed with aqueous
saturated sodium bicarbonate solution and dried, then concentrated to
give pure 3. If necessary, the product was purified using column chro-
matography on silica gel to give pure quinone. The alkaline solution
was acidified by 10% hydrochloric acid solution and extracted with
ethyl acetate. The organic layer was washed with aqueous sodium thio-
sulfate solution and dried, then concentrated to recover 1 (75—85%)
which was purified by recrystallization from diethyl ether–hexane. All
new compounds gave satisfactory spectrospecific data.
32) It remains unclear whether iodine(V) or iodine(III) species was formed
during the reaction. The experiment of 1H-NMR of a mixture of 1 and
an excess Oxone® in CD3CN–D2O showed no presence of hypervalent
iodine species.
33) Many reports for the formation of hypervalent iodine species by the
oxidation of iodoarene with Oxone® have appeared.36—41)
34) Compound 9: yellow crystals, mp 46—47 °C (hexane). 1H-NMR
(300 MHz, CDCl3) d: 0.99 (6H, d, Jꢀ6.6 Hz), 2.07—2.22 (1H, m),
2.30 (2H, d, Jꢀ6.9 Hz), 5.00 (2H, d, Jꢀ1.9 Hz), 6.69 (1H, br q,
Jꢀ2.0 Hz), 6.77 (1H, d, Jꢀ10.0 Hz), 6.80 (1H, dd, Jꢀ10.0, 1.0 Hz).
13C-NMR (75 MHz, CDCl3) d: 22.5 (2), 25.7, 43.1, 59.2, 131.3, 136.3,
136.4, 143.1, 171.9, 185.9, 186.7. IR (KBr) cmꢁ1: 1744, 1648. MS
(EI) m/z: 222 (Mꢂ). HR-MS (EI) m/z: 222.08822 (Calcd for C12H14O4:
222.08921).
35) Although Nojima et al. reported oxidation of 8 with CAN, that report
includes no description related to detailed reaction conditions and
yield.7)
36) Frigerio M., Santagostino M., Sputore S., J. Org. Chem., 64, 4537—
4538 (1999).
37) Mülbaier M., Giannis A., Angew. Chem. Int. Ed., 40, 4393—4394
(2001).
38) Mülbaier M., Giannis A., ARKIVOC, 2003(Vi), 228—236 (2003).
39) Ladziata U., Willging J., Zhdankin V. V., Org. Lett., 8, 167—170
(2006).
40) Koposov A. Y., Litvinov D. N., Zhdankin V. V., Ferguson M. J., Mc-
Donald R., Tykwinski R. R., Eur. J. Org. Chem., 2006, 4791—4795
(2006).
41) Karimov R. R., Kazhkenov Z.-G. M., Modjewski M. J., Peterson E.
M., Zhdankin V. V., J. Org. Chem., 72, 8149—8151 (2007).
28) Schulze A., Giannis A., Synthesis, 2006, 257—260 (2006).