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egy, stereoselective synthesis of highly functionalized ABC ring
system, stereoselective glycosylation of a tertiary alcohol with a
2,3-deoxy-sugar, and Michael–Dieckmann type condensation with
thioester. These strategies and methodologies realized the
straightforward synthesis of lactonamycin (1).
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Board, J. J. Org. Chem. 2007, 72, 1395–1398; (b) Parsons, P. J.; Board, J.; Waters,
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M. J. Org. Chem. 2006, 71, 8151–8158; (e) Vézouët, R. L.; White, A. J. P.; Burrows,
J. N.; Barett, A. G. M. Tetrahedron 2006, 62, 12252–12263; (f) Kelly, T. R.; Cai, X.;
Tu, B.; Elliot, E. L.; Grossmann, G.; Laurent, P. Org. Lett. 2004, 6, 4953–4956; (g)
Kelly, T. R.; Xu, D.; Martínez, G.; Wang, H. Org. Lett. 2002, 4, 1527–1529; (h)
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S. J. Angew. Chem., Int. Ed. 2003, 42, 5625–5629; (b) Siu, T.; Cox, C. D.;
Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 5629–5634.
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7. Crystallographic data (excluding structure factors) for the structures of ( )-2
and 25b have been deposited with the Cambridge Crystallographic Data Center
as supplementary publication numbers CCDC 770402 for ( )-2 and 770403 for
25b.
Acknowledgments
Special thanks to Dr. Yoshikazu Takahashi in Microbial Chemis-
try Research Center for providing natural lactonamycin. The
authors thank Mr. Kunitoshi Takeda and Ms. Utako Furukawa for
preliminary studies. This work was financially supported by the
Consolidated Research Institute for Advanced Science and Medical
Care, the Global COE program ‘Center for Practical Chemical Wis-
dom’, and the Scientific Research on Priority Area ‘Creation of Bio-
logically Functional Molecules’ from the Ministry of Education,
Culture, Sports, Science and Technology.
Supplementary data
Supplementary data (the spectrum data of compounds ( )-2, 3,
4a, 8, 9, 10, 15, 16, 19, 20, 21, 25a, 27 and synthetic lactonamycin
(1), and 1H NMR spectrum (600 MHz in CDCl3) and 13C NMR spec-
trum (150 MHz in CDCl3) of synthetic lactonamycin (1)) associated
with this article can be found, in the online version, at doi:10.1016/
8. (a) Servi, S. J. Org. Chem. 1985, 50, 5865–5867; (b) Hanes, A. H. Carbohydr. Res.
1972, 21, 99–109.
9. Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503–1531.
10. Recent reviews for Michael–Dieckmann type annulation: (a) Mal, D.; Pahari, P.
Chem. Rev. 2007, 107, 1892–1918; (b) Tatsuta, K.; Hosokawa, S. Chem. Rec.
2006, 6, 217–233; (c) Tatsuta, K.; Hosokawa, S. Sci. Tech. Adv. Mater 2006, 7,
397–410; (d) Tatsuta, K.; Hosokawa, S. Chem. Rev. 2005, 105, 4707–4729.
11. The authentic sample of the natural product was provided by Dr. Yoshikazu
Takahashi in Microbial Chemistry Research Center and purified by our
References and notes
procedures:
½
a 2D6
ꢂ
þ 45ꢃ (c 0.22, MeCN), mp 103–107 °C (decomp.). The
1. (a) Matsumoto, N.; Tsuchida, T.; Maruyama, M.; Sawa, R.; Kinoshita, N.;
Homma, Y.; Takahashi, Y.; Iinuma, H.; Naganawa, H.; Sawa, T.; Hamada, M.;
decomposition was observed by using a polarization microscope.