1500
B. Lee et al.
LETTER
Korean Chem. Soc. 2006, 27, 463. (e) Yu, C.-M.; Youn, J.;
Lee, M.-K. Org. Lett. 2005, 7, 3733. (f) Yu, C.-M.; Youn,
J.; Hong, Y.-T.; Yoon, S.-K. Org. Lett. 2005, 7, 4507.
(g) Yu, C.-M.; Hong, Y.-T.; Lee, J. J. Org. Chem. 2004, 69,
8506.
O
OsO4 (3 mol%)
KIO4
R
HN
R
HN
THF–H2O (3:1)
H
H
(4) (a) Tursch, B.; Braekman, J.-C.; Daloze, D.; Hootele, C.;
Losman, D.; Karlsson, R.; Pasteels, J.-M. Tetrahedron Lett.
1973, 201. (b) Lognay, G.; Hemptinne, J. L.; Chan, F. Y.;
Gaspar, C. H.; Marlier, M.; Braekman, J. C.; Daloze, D.;
Pasteels, J. M. J. Nat. Prod. 1996, 59, 510.
(5) (a) Hart, N. K.; Johns, S. R.; Lamberton, J. A. Aust. J. Chem.
1967, 20, 561. (b) Brown, W. V.; Moore, B. P. Aust. J.
Chem. 1982, 35, 1255. (c) Eisner, T.; Goetz, M.;
Aneshausley, D.; Ferstandig-Arnold, G.; Meinwald, J.
Experientia 1986, 42, 204.
9
1 R = n-C5H11, 64%
2 R = Me, 71%
Ac2O,
pyridine
9a
O
i. O3
ii. Me2S
n-C5H11
AcN
n-C5H11
AcN
H
–78 °C, CH2Cl2
H
10a
11a 63%
(6) For a review, see: King, A. G.; Meinwald, J. Chem. Rev.
1996, 96, 1105.
Scheme 4
(7) (a) Itoh, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4,
2469. (b) Mechelke, M. F.; Meyers, A. I. Tetrahedron Lett.
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J.; Husson, H.-P. J. Org. Chem. 1992, 57, 4211.
(8) (a) Kang, K.-T.; U, J. S.; Park, D.; Kim, J. G.; Kim, W. J.
Bull. Korean Chem. Soc. 1995, 16, 464. (b) Keck, G. E.;
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(c) Keck, G. E.; Truong, A. P. Org. Lett. 2005, 7, 2153.
(d) Wender, P. A.; Verma, V. A. Org. Lett. 2008, 10, 3331.
(e) Kang, K.-T.; Sung, T. M.; Jung, H. C.; Lee, J. G. Bull.
Korean Chem. Soc. 2008, 29, 1669.
(9) (a) Yu, C.-M.; Choi, H.-S.; Lee, J.-K.; Yoon, S.-K. J. Org.
Chem. 1997, 62, 6687. (b) Yu, C.-M.; Jung, W.-H.; Choi,
H.-S.; Lee, J.; Lee, J.-K.; Yoon, S.-K. Tetrahedron Lett.
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(10) (a) Mitsunobu, O. Synthesis 1981, 1. (b) Dembinski, R. Eur.
J. Org. Chem. 2004, 2763.
Acknowledgment
Generous financial support from the Korea Research Foundation
(KRF-2006-312-C00234; KRF-2005-005-J11901) and the Korea
Science & Engineering Foundation (R01-2007-000-20315-0) is
gratefully acknowledged.
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Synlett 2009, No. 9, 1498–1500 © Thieme Stuttgart · New York