Abstract
Duocarmycin A, duocarmycin SA, (+)-CC-1065, and (+)-yatakemycin are site-selective DNA alkylating agents isolated from Streptomyces sp. In addition to their significant biological activity, their characteristic structural features, which arise from the presence of both the cyclopropapyrroloindole motif, responsible for the DNA alkylation, and a highly functionalized heterocyclic segment that acts as a DNA-binding site, have attracted a great deal of attention from the synthetic community. To date, a number of total syntheses as well as numerous synthetic studies on the partial structures of these compounds have been reported. In particular, over the last 15 years, a series of synthetic strategies and tactics have emerged, and remarkable progresses have been made in this area. Since several reviews on the biological function of these compounds have been already reported, this chapter mainly deals with selected examples on their representative total syntheses.
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Abbreviations
- Ac:
-
Acetyl
- Bn:
-
Benzyl
- Boc:
-
tert-Butoxycarbonyl
- Bu:
-
Butyl
- Cbz:
-
Benzyloxycarbonyl
- dba:
-
Dibenzylideneacetone
- DMAP:
-
4-(N,N-Dimethylamino)pyridine
- DMF:
-
N,N-Dimethylformamide
- DMSO:
-
Dimethyl sulfoxide
- Fmoc:
-
9-Fluorenylmethyloxycarbonyl
- HOBt:
-
1-Hydroxybenzotriazole
- Ms.:
-
Methanesulfonyl
- Ns:
-
2-Nitrobenzenesulfonyl
- Ph:
-
Phenyl
- PPTS:
-
Pyridinium p-toluenesulfonate
- quant:
-
Quantitative
- TBAF:
-
Tetra-n-butylammonium fluoride
- TBS:
-
tert-Butyldimethylsilyl
- Tf:
-
Trifluoromethanesulfonyl
- TFA:
-
Trifluoroacetic acid
- THF:
-
Tetrahydrofuran
- TMG:
-
1,1,3,3-Tetramethylguanidine
- TMP:
-
2,2,6,6-Tetramethylpiperidine
- TMS:
-
Trimethylsilyl
- TPAP:
-
Tetra-n-propylammonium perruthenate
- Troc:
-
2,2,2-Trichloroethoxycarbonyl
- WSCD:
-
Water-soluble carbodiimide
References
L.J. Hanka, A. Dietz, S.A. Gerpheide, S.L. Kuentzel, D.G. Martin, J. Antibiot. 31, 1211 (1978)
D.G. Martin, C. Biles, S.A. Gerpheide, L. J. Hanka, W.C. Krueger, J.P. McGovren, S.A. Mizsak, G.L. Neil, J. C. Stewart, J. Visser, J. Antibiot. 34, 1119 (1981)
I. Takahashi, K. Takahashi, M. Ichimura, M. Morimoto, K. Asano, I. Kawamoto, F. Tomita, H. Nakano, J. Antibiot. 41, 1915 (1988)
T. Yasuzawa, K. Muroi, M. Ichimura, I. Takahashi, T. Ogawa, K. Takahashi, H. Sano, Y. Saitoh, Chem. Pharm. Bull. 43, 378 (1995)
K. Ohba, H. Watanabe, T. Sasaki, Y. Takeuchi, Y. Kodama, T. Nakazawa, H. Yamamoto, T. Shomura, M. Sezaki, S. Kondo, J. Antibiot. 41, 1515 (1988)
S. Ishii, M. Nagasawa, Y. Kariya, H. Yamamoto, S. Inouye, S. Kondo, J. Antibiot. 42, 1713 (1989)
M. Ichimura, T. Ogawa, K. Takahashi, E. Kobayashi, I. Kawamoto, T. Yasuzawa, I. Takahashi, H. Nakano, J. Antibiot. 43, 1037 (1990)
M. Ichimura, T. Ogawa, S. Katsumata, K. Takahashi, I. Takahashi, H. Nakano, J. Antibiot. 44, 1045 (1991)
Y. Igarashi, K. Futamata, T. Fujita, A. Sekine, H. Senda, H. Naoki, T. Furumai, J. Antibiot. 56, 107 (2003)
L. H. Hurley, D.R.N.-VanDevanter, Acc. Chem. Res. 19, 230 (1986)
D.L. Boger, Acc. Chem. Res. 28, 20 (1995)
D.L. Boger, D.S. Johnson, Angew. Chem. Int. Ed. Engl. 35, 1438 (1996)
J.P. Parrish, D.B. Kastrinsky, S.E. Wolkenberg, Y. Igarashi, D.L. Boger, J. Am. Chem. Soc. 125, 10971 (2003)
D.L. Boger, R.M. Garbaccio, Acc. Chem. Res. 32, 1043 (1999)
V.H. Rawal, M.P. Cava, J. Am. Chem. Soc. 108, 2110 (1986)
D.L. Boger, R.S. Coleman, Tetrahedron Lett. 28, 1027 (1987)
D.L. Boger, R.S. Coleman, J. Am. Chem. Soc. 109, 2717 (1987)
P. Martin, Helv. Chim. Acta, 72, 1554 (1989)
K. Okano, N. Mitsuhashi, H. Tokuyama, Chem. Commun. 46, 2641 (2010)
K. Okano, N. Mitsuhashi, H. Tokuyama, Tetrahedron 69, 10946 (2013)
D.L. Boger, C.W. Boyce, R.M. Garbaccio, J.A. Goldberg, Chem. Rev. 97, 787 (1997)
K. Yamada, T. Kurokawa, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 125, 6630 (2003)
K. Yamada, T. Kubo, H. Tokuyama, T. Fukuyama, Synlett 2, 231 (2002)
Y. Fukuda, K. Nakatani, Y. Ito, S. Terashima, Tetrahedron Lett. 31, 6699 (1990)
M.S. Tichenor, D.B. Kastrinsky, D.L. Boger, J. Am. Chem. Soc. 126. 8396 (2004)
L.F. Tietze, F. Haunert, T. Feuerstein, T. Herzig, Eur. J. Org. Chem. 562 (2003)
R.E. Bolton, C.J. Moody, C.W. Rees, G.J. Tojo, J. Chem. Soc., Perkin Trans. 1, 931 (1987)
M.S. Tichenor, J.D. Trzupek, D.B. Kastrinsky, F. Shiga, I. Hwang, D.L. Boger, J. Am. Chem. Soc. 128, 15683 (2006)
K. Okano, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 128, 7136 (2006)
K. Okano, K. Okuyama, T. Fukuyama, H. Tokuyama, Synlett 13, 1977 (2008)
Y. Enomoto, Y. Furutani, H. Naganawa, M. Hamada, T. Takeuchi, H. Umezawa, Agric. Biol. Chem. 42, 1331 (1978)
H. Nakamura, Y. Enomoto, T. Takeuchi, H. Umezawa, Y. Iitaka, Agric. Biol. Chem. 42, 1337 (1978)
N. Komoto, Y. Enomoto, M. Miyagaki, Y. Tanaka, K. Nitanai, H. Umezawa, Agric. Biol. Chem. 43, 555 (1979)
N. Komoto, Y. Enomoto, Y. Tanaka, K. Nitanai, H. Umezawa, Agric. Biol. Chem. 43, 559 (1979)
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Sakata, J., Tokuyama, H. (2019). Recent Progress on the Total Synthesis of Duocarmycins A and SA, Yatakemycin, and PDE-I and PDE-II. In: Kobayashi, Y. (eds) Cutting-Edge Organic Synthesis and Chemical Biology of Bioactive Molecules. Springer, Singapore. https://doi.org/10.1007/978-981-13-6244-6_5
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DOI: https://doi.org/10.1007/978-981-13-6244-6_5
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