Useful Synthetic Method for Lactones
Recently, Shiina et al. have been reported a new condensation method using dehydrating condensing agents 1 and 2. In the presence of 1 or 2, carboxylic acids react with nearly equimolar amounts of alcohols or amines to obtain corresponding carboxylic esters or amides in high yields.
1 and 2 perform effectively under Lewis acidic conditions and basic conditions, respectively. Therefore, a wide variety of substrates can be used by choosing 1 and 2.
This method also applies to intramolecular reactions. For example, 1 and 2 have been used the synthesis of the lactone moieties of cephalosporolide D and octalactin B, respectively.
1 and 2 are easy to handle, and condensation reactions using these reagents in this simple procedure have obtained desired products in high yields. 1 and 2 are quite effective as dehydrating condensing agents in the synthesis of carboxylic esters and amides, especially, when synthesizing lactones and lactams.
- 1)Condensation reaction by using 4-trifluoromethylbenzoic anhydride
- a)I. Shiina, S. Miyoshi, M. Miyashita, T. Mukaiyama, Chem. Lett. 1994, 23, 515.
- b)I. Shiina, M. Miyashita, M. Nagai, T. Mukaiyama, Heterocycles 1995, 40, 141.
- c)I. Shiina, H. Fujisawa, T. Ishii, Y. Fukuda, Heterocycles 2000, 52, 1105.
- d)I. Shiina, Tetrahedron 2004, 60, 1587.
- 2)Condensation reaction by using 2-methyl-6-nitrobenzoic anhydride
- a)I. Shiina, R. Ibuka, M. Kubota, Chem. Lett. 2002, 31, 286.
- b)J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Org. Lett. 2003, 5, 3021.
- c)I. Shiina, H. Oshiumi, M. Hashizume, Y. Yamai, R. Ibuka, Tetrahedron Lett. 2004, 45, 543.
- d)I. Shiina, Tetrahedron 2004, 60, 4729.
- e)I. Shiina, M. Kubota, H. Oshiumi, M. Hashizume, J. Org. Chem. 2004, 69, 1822.
- f)I. Shiina, M. Hashizume, Y. Yamai, H. Oshiumi, T. Shimazaki, Y. Takasuna, R. Ibuka, Chem. Eur. J. 2005, 11, 6601.
- g)Tokyo Kasei Kogyo Co., Ltd, JP Patent 2003-335731.
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