H. Seto, Org. Lett., 2002, 4, 3819; (e) P. A. Wender and
K. E. Longcore, Org. Lett., 2009, 11, 5474.
4 (a) H. Wehlan, M. Dauber, M. T. Mujica Fernaud,
J. Schuppan, R. Mahrwald, B. Ziemer, M. E. Juarez Garcia
and U. Koert, Angew. Chem., Int. Ed., 2004, 43, 4597;
(b) K. C. Nicolaou, Y. Li, K. Sugita, H. Monenschein,
P. Guntupalli, H. J. Mitchell, K. C. Fylaktakidou,
D. Vourloumis, P. Giannakakou and A. O’Brate, J. Am. Chem.
Soc., 2003, 125, 15443; (c) M. T. Crimmins, H. S. Christie,
A. Long and K. Chaudhary, Org. Lett., 2009, 11, 831.
5 (a) K. C. Nicolaou, Y. Li, K. C. Fylaktakidou, H. J. Mitchell,
H.-X. Wei and B. Weyershausen, Angew. Chem., Int. Ed., 2001, 40,
3849; (b) M. T. Crimmins and A. Long, Org. Lett., 2005, 7, 4157;
(c) M. Handa, W. J. Smith, III and W. R. Roush, J. Org. Chem.,
2008, 73, 1036.
Scheme 4 Preparation of 6.
6 (a) A. R. Salomon, D. W. Voehringer, L. A. Herzenberg and
C. Khosla, Proc. Natl. Acad. Sci. U. S. A., 2000, 97, 14766;
(b) A. R. Salomon, D. W. Voehringer, L. A. Herzenberg and
C. Khosla, Chem. Biol., 2001, 8, 71.
7 Y. Kim and P. L. Fuchs, Org. Lett., 2007, 9, 2445.
8 D. Horton, W. Priebe and O. Varela, Carbohydr. Res., 1985, 144,
317.
9 S. Czernecki, K. Vijayakumaran and G. Ville, J. Org. Chem., 1986,
51, 5472.
10 (a) G. Jung and A. Klemer, Chem. Ber., 1981, 114, 740;
(b) K. A. Parker and S. M. Meschwitz, Carbohydr. Res., 1988,
172, 319; (c) T. Kauffmann, W. Klaffke, C. Philipp and J. Thiem,
Carbohydr. Res., 1990, 207, 33.
11 (a) J. A. Katzenellenbogen and S. B. Bowlus, J. Org. Chem., 1973,
38, 627; (b) S. B. Bowlus and J. A. Katzenellenbogen, J. Org.
Chem., 1974, 39, 3309; (c) T. Nakata, T. Tanaka and T. Oishi,
Tetrahedron Lett., 1983, 24, 2653; (d) N. Bajwa and M. P. Jennings,
J. Org. Chem., 2008, 73, 3638.
Scheme 5 Preparation of sugar 26.
12 For a report on intramolecular methyl delivery to an adjacent
epoxide via trimethylalkoxyalanate(IV), see: M. Sasaki, K. Tanino
and M. Miyashita, Org. Lett., 2001, 3, 1765.
13 For diastereoselective 1,4-addition of methyl group to a quinol
system via trimethylalkoxyalanate(IV), see: (a) M. C. Carreno,
M. Perez-Gonzalez, M. Ribagorda and K. N. Houk, J. Org.
Chem., 1998, 63, 3687; (b) M. C. Carreno, M. Perez-Gonzalez,
M. Ribagorda and J. Fisher, J. Org. Chem., 1996, 61, 6758;
(c) V. Rodeschini, J.-G. Boiteau, P. Van de Weghe, C. Tarnus
and J. Eustache, J. Org. Chem., 2003, 69, 357.
14 T. S. Pritytskaya, S. V. Sviridov and T. K. Morozova, Zh. Obshch.
Khim., 1987, 57, 839.
15 For a related glycosylation, see: D. Hou and T. L. Lowary, J. Org.
Chem., 2009, 74, 2278.
Scheme 6 Synthesis of glycosyl donor 5.
16 (a) S. Hanessian, Carbohydr. Res., 1966, 4, 86; (b) D. L. Failia,
T. L. Hullar and S. B. Siskin, Chem. Commun., 1966, 716;
(c) S. Hanessian and N. R. Pleassas, J. Org. Chem., 1969, 34,
1035, 1045, 1053; (d) T. L. Hullar and S. B. J. Siskin, J. Org.
Chem., 1970, 35, 225.
17 K. Tori, T. That Thang, M. Sangare and G. Lukacs, Tetrahedron
Lett., 1977, 18, 717.
18 R. Filler, Chem. Rev., 1963, 63, 21.
19 (a) H.-M. Liu, Y. Sato and Y. Tsuda, Chem. Pharm. Bull., 1993,
41, 491; (b) F. W. Lichtenthaler and P. Jarglis, Chem. Ber., 1980,
´
113, 489; (c) C. D. Warren, C. Auge, M. L. Laver, S. Suzuki,
D. Power and R. Jeanloz, Carbohydr. Res., 1980, 82, 71;
(d) D. C. Baker, D. Horton and C. G. Tindall, Jr., Carbohydr.
Res., 1972, 24, 192; (e) M. Mori and S. Tejima, Chem. Pharm. Bull.,
1983, 31, 1593; (f) H. Tian, X. She and Y. Shi, Org. Lett., 2001, 3,
715; (g) M. A. Mortellaro, S. Hong, D. T. Winn and
A. W. Czarnik, Bioorg. Med. Chem. Lett., 1994, 4, 2041.
20 J. Tormo and G. C. Fu, Org. Syn., 2002, 78, 239.
and the iodo groups were removed in one pot using tributyltin
hydride to provide 26 in 88% yield.25
Reduction of 26 under Pd/H2 conditions followed by the
fluorination of lactol 27 with diethylamino sulfur trifluoride26
(DAST) provided the glycosidic donor 5 in 81% yield but
required chromatography (Scheme 6). A more effective fluori-
nating agent, XtalFluor-Es 28 was recently reported.27 Fluori-
nation of lactol 27 by this reagent provided the fluoride 5 in
excellent yield with no side products, thus eliminating the need
for chromatography.
The synthesis of 5 was completed in 10% yield over 16 linear
steps. Studies on O-27 glycosylation of the glycosyl fluoride 5
are currently under investigation.
21 H. G. Kuivila, Acc. Chem. Res., 1968, 1, 299.
Notes and references
22 P. Renaud and M. Gerster, Angew. Chem., Int. Ed., 1998, 37, 2562.
23 H. S. Park, H. Y. Lee and Y. H. Kim, Org. Lett., 2005, 7, 3187.
24 R. Preuss and R. R. Schmidt, Synthesis, 1988, 694.
25 D. H. R. Barton and S. W. McCombie, J. Chem. Soc., Perkin
Trans. 1, 1975, 16, 1574.
1 J. W. Kim, H. Adachi, K. Shin-ya, Y. Hayakawa and H. Seto,
J. Antibiot. (Tokyo), 1997, 50(7), 628.
2 For a recent review see: P. T. Daniel, U. Koert and J. Schuppan,
Angew. Chem., Int. Ed., 2006, 45, 872.
3 (a) P. A. Wender, M. Sukopp and K. Longcore, Org. Lett., 2005, 7,
3025; (b) P. A. Wender and K. E. Longcore, Org. Lett., 2009, 11,
5474; (c) P. A. Wender and K. E. Longcore, Org. Lett., 2007, 9,
691; (d) P. A. Wender, A. V. Gulledge, O. D. Jankowski and
26 W. J. Middleton, J. Org. Chem., 1975, 40, 574.
27 A. L’Heureux, F. Beaulieu, C. Bennett, D. R. Bill, S. Clayton,
F. o. LaFlamme, M. Mirmehrabi, S. Tadayon, D. Tovell and
M. Couturier, J. Org. Chem., 2010, 75, 3401.
c
5860 Chem. Commun., 2011, 47, 5858–5860
This journal is The Royal Society of Chemistry 2011