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Volumn 46, Issue 31, 2007, Pages 5934-5937

Solid-phase synthesis of epigallocatechin gallate derivatives

Author keywords

Catechins; Combinatorial chemistry; Etherification; Natural products; Solid phase synthesis

Indexed keywords

ACETIC ACID; POLYSTYRENES; SYNTHESIS (CHEMICAL);

EID: 34547809453     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701276     Document Type: Article
Times cited : (32)

References (21)
  • 14
    • 33750355952 scopus 로고    scopus 로고
    • The same type of reductive etherification was applied to the solution-phase stereoselective synthesis of trans- and cis-2,4-substituted benzopyran derivatives. The stereoselectivity of benzopyran formation was controlled by the bulkiness of the reducing reagents: K. Li, K. Vanka, W. H. Thompson, J. A. Tunge, Org. Lett. 2006, 8, 4711-4714
    • The same type of reductive etherification was applied to the solution-phase stereoselective synthesis of trans- and cis-2,4-substituted benzopyran derivatives. The stereoselectivity of benzopyran formation was controlled by the bulkiness of the reducing reagents: K. Li, K. Vanka, W. H. Thompson, J. A. Tunge, Org. Lett. 2006, 8, 4711-4714.
  • 16
    • 34547736998 scopus 로고    scopus 로고
    • We first attempted to synthesize the solid-supported α- hydroxyketone by rhodium-catalyzed reduction of the solid-supported enone derivative with triethylsilane to provide the silyl enol ether, followed by oxidation of the vinyl ether with dimethyldioxirane. However, this approach did not work well, as the reactions should be carried out in polar solvents, such as acetone, at low temperature, 78 °C, and these conditions are not suitable for synthesis on a solid support
    • We first attempted to synthesize the solid-supported α- hydroxyketone by rhodium-catalyzed reduction of the solid-supported enone derivative with triethylsilane to provide the silyl enol ether, followed by oxidation of the vinyl ether with dimethyldioxirane. However, this approach did not work well, as the reactions should be carried out in polar solvents, such as acetone, at low temperature (-78 °C), and these conditions are not suitable for synthesis on a solid support.
  • 19
    • 0035945009 scopus 로고    scopus 로고
    • Odorless 1-dodecanethiol is easy to use: M. Node, K. Kumar, K. Nishide, S. Ohsugi, T. Miyamoto, Tetrahedron Lett. 2001, 42, 9207-9210.
    • Odorless 1-dodecanethiol is easy to use: M. Node, K. Kumar, K. Nishide, S. Ohsugi, T. Miyamoto, Tetrahedron Lett. 2001, 42, 9207-9210.
  • 20
    • 34547735990 scopus 로고    scopus 로고
    • The library of protected epicatechins was suitable for stock. The deprotected derivatives were not sufficiently stable to be stored for long periods
    • The library of protected epicatechins was suitable for stock. The deprotected derivatives were not sufficiently stable to be stored for long periods.
  • 21
    • 34547762229 scopus 로고    scopus 로고
    • In our first attempt at the library synthesis we used 30 mg of the resin fully packed in MicroKans. The synthesis failed because the packing of the resin in MicroKans reduced the reactivity of the substrates on the resin, especially toward epoxidation. The mobility of the resin in the reaction mixture is an important factor in solid-phase synthesis. MiniKans, on the other hand, are amenable to the use of 100 mg of a resin
    • In our first attempt at the library synthesis we used 30 mg of the resin fully packed in MicroKans. The synthesis failed because the packing of the resin in MicroKans reduced the reactivity of the substrates on the resin, especially toward epoxidation. The mobility of the resin in the reaction mixture is an important factor in solid-phase synthesis. MiniKans, on the other hand, are amenable to the use of 100 mg of a resin.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.