692
J. Mulzer et al.
CLUSTER
O
O
OH
Me
Me
Me
Me
Me
OH
Me
HO
Me
Me
Et
OAc
Me
OH
Me
OMe
Me
NMe2
Me
HO
O
O
O
O
O
O
3
3
Me
OMe
OH
O
O
O
O
Me
Me
Me
Me
OH
4
O
O
Me
Me
OAc
Lankamycin
[3-(4-O-acetyl)-L-arcanosyl]
Erythromycin D
(3-L-mycarosyl)
Figure 8
(5) Otake, N.; Koenuma, M.; Miyamae, H.; Sato, S.; Saito, Y.
Tetrahedron Lett. 1975, 16, 4147.
(12) Braun, M. Stereoselective Synthesis, In Houben–Weyl,
Methods of Organic Synthesis, Vol. E 21b; Helmchen, G.;
Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme:
Stuttgart, 1995, 1644–1656.
(13) Paul, R.; Tschetichoff, S. Bull. Soc. Chim. Fr. 1948, 197.
(14) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem.
Soc. 1988, 110, 3560.
(15) Corey, E. J.; Helal, C. J. Angew. Chem. Int. Ed. 1998, 37,
1986; Angew. Chem. 1998, 110, 2092.
(16) (a) Schummer, D.; Irschik, H.; Reichenbach, H.; Höfle, G.
Liebigs Ann. Chem. 1994, 283. (b) Total synthesis: Mulzer,
J.; Berger, M. J. Org. Chem. 2004, 69, 891.
(17) Corcoran, J. W.; Chick, M. In Biosynthesis of Antibiotics;
Snell, J. F., Ed.; Academic Press: New York, 1966.
(18) Keller-Schierlein, W.; Roncari, G. Helv. Chim. Acta 1962,
45, 138.
(19) Total syntheses of optically active mycarose: (a) Korte, F.;
Claussen, U.; Göhring, K. Tetrahedron 1962, 18, 1257.
(b) Lemal, D. M.; Pacht, P. D.; Woodward, R. B.
Tetrahedron 1962, 18, 1275. (c) Tatsuta, K.; Mukayama, S.;
Toshima, K.; Yoshida, T. Carbohydr. Res. 1991, 222, 173.
(d) Flaherty, B.; Overend, W. G.; Williams, N. R. J. Chem.
Soc. C 1966, 398. (e) Koft, E.; Dorff, P.; Kullnig, R. J. Org.
Chem. 1989, 54, 2936.
(6) Confer: (a) Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi,
Y. J. Am. Chem. Soc. 1979, 101, 259. (b) Fukuyama, T.;
Wang, C. L. J.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 260.
(c) Fukuyama, T.; Akasaka, K.; Karanewsky, D. S.; Wang,
C. L. J.; Schmid, G.; Kishi, Y. J. Am. Chem. Soc. 1979, 101,
262.
(7) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
(8) Evans, D. A.; Miller, S. J.; Ennis, M. D. J. Org. Chem. 1993,
58, 471.
(9) (a) Isolation: Gräfe, U.; Schade, W.; Roth, M.; Radics, L.;
Incze, M.; Ujszaszy, K. J. Antibiot. 1984, 37, 836. (b) See
also: Brooks, H. A.; Gardner, D.; Poyser, J. P.; King, T. J. J.
Antibiot. 1984, 37, 1501. (c) Total syntheses: Danishefsky,
S. J.; Selnick, H. G.; Zelle, R. E.; DeNinno, M. P. J. Am.
Chem. Soc. 1988, 110, 4368. (d) See further: Defosseux,
M.; Blanchard, N.; Meyer, C.; Cossy, J. J. Org. Chem. 2004,
69, 4626. (e) Komatsu, K.; Tanino, K.; Miyashita, M.
Angew. Chem. Int. Ed. 2004, 43, 4341; Angew. Chem. 2004,
116, 4441.
(10) Mitsunobu, O. Synthesis 1981, 1.
(11) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc.
1990, 112, 6348.
(20) Keller-Schierlein, W.; Roncari, G. Helv. Chim. Acta 1966,
49, 705.
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