메뉴 건너뛰기




Volumn 6, Issue 7, 2004, Pages 1103-1106

Efficient solid-phase synthesis of clavulones via sequential coupling of α- and ω-chains

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CLAVULONE DERIVATIVE; TETRAHYDROPYRANYL ETHER;

EID: 2342533642     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036361b     Document Type: Article
Times cited : (19)

References (45)
  • 4
    • 0036603591 scopus 로고    scopus 로고
    • For a recent review of the synthesis of a natural product-like library, see: (a) Nielsen, J. Curr. Opin. Chem. Biol. 2002, 6, 297-305.
    • (2002) Curr. Opin. Chem. Biol. , vol.6 , pp. 297-305
    • Nielsen, J.1
  • 5
    • 0033591904 scopus 로고    scopus 로고
    • For our reports of the combinatorial synthesis of small-molecule libraries based on the structure of biologically active natural products, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716-3722. Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (e) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 1159-1162. (f) Tanaka, H.; Moriwaki, M.; Takahashi, M. Org. Lett. 2003, 5, 3807-3809. (g) Tanaka, H.; Amaya, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 3053-3057. (h) Takahashi, T.; Nagamiya, H.; Doi, T.; Peter, G.; Griffiths, P. G.; Bray, A. M. J. Comb. Chem. 2003, 5, 414-428. Takahashi, T.; Kusaka, S.; Doi, T.; Sunazuka, T.; Omura, S. Angew. Chem., Int. Ed. 2003, 42, 5230-5234.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 6749-6750
    • Doi, T.1    Hijikuro, I.2    Takahashi, T.3
  • 6
    • 0034835668 scopus 로고    scopus 로고
    • For our reports of the combinatorial synthesis of small-molecule libraries based on the structure of biologically active natural products, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716-3722. Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (e) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 1159-1162. (f) Tanaka, H.; Moriwaki, M.; Takahashi, M. Org. Lett. 2003, 5, 3807-3809. (g) Tanaka, H.; Amaya, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 3053-3057. (h) Takahashi, T.; Nagamiya, H.; Doi, T.; Peter, G.; Griffiths, P. G.; Bray, A. M. J. Comb. Chem. 2003, 5, 414-428. Takahashi, T.; Kusaka, S.; Doi, T.; Sunazuka, T.; Omura, S. Angew. Chem., Int. Ed. 2003, 42, 5230-5234.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3716-3722
    • Hijikuro, I.1    Doi, T.2    Takahashi, T.3
  • 7
    • 0034935552 scopus 로고    scopus 로고
    • For our reports of the combinatorial synthesis of small-molecule libraries based on the structure of biologically active natural products, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716-3722. (c) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (e) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 1159-1162. (f) Tanaka, H.; Moriwaki, M.; Takahashi, M. Org. Lett. 2003, 5, 3807-3809. (g) Tanaka, H.; Amaya, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 3053-3057. (h) Takahashi, T.; Nagamiya, H.; Doi, T.; Peter, G.; Griffiths, P. G.; Bray, A. M. J. Comb. Chem. 2003, 5, 414-428. Takahashi, T.; Kusaka, S.; Doi, T.; Sunazuka, T.; Omura, S. Angew. Chem., Int. Ed. 2003, 42, 5230-5234.
    • (2001) Synlett , pp. 1101-1104
    • Matsuda, A.1    Doi, T.2    Tanaka, H.3    Takahashi, T.4
  • 8
    • 0036377086 scopus 로고    scopus 로고
    • For our reports of the combinatorial synthesis of small-molecule libraries based on the structure of biologically active natural products, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716-3722. (c) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (d) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (e) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 1159-1162. (f) Tanaka, H.; Moriwaki, M.; Takahashi, M. Org. Lett. 2003, 5, 3807-3809. (g) Tanaka, H.; Amaya, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 3053-3057. (h) Takahashi, T.; Nagamiya, H.; Doi, T.; Peter, G.; Griffiths, P. G.; Bray, A. M. J. Comb. Chem. 2003, 5, 414-428. Takahashi, T.; Kusaka, S.; Doi, T.; Sunazuka, T.; Omura, S. Angew. Chem., Int. Ed. 2003, 42, 5230-5234.
    • (2002) Synlett , pp. 1427-1430
    • Tanaka, H.1    Zenkoh, T.2    Setoi, H.3    Takahashi, T.4
  • 9
    • 0037925396 scopus 로고    scopus 로고
    • For our reports of the combinatorial synthesis of small-molecule libraries based on the structure of biologically active natural products, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716-3722. (c) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (d) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (e) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 1159-1162. (f) Tanaka, H.; Moriwaki, M.; Takahashi, M. Org. Lett. 2003, 5, 3807-3809. (g) Tanaka, H.; Amaya, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 3053-3057. (h) Takahashi, T.; Nagamiya, H.; Doi, T.; Peter, G.; Griffiths, P. G.; Bray, A. M. J. Comb. Chem. 2003, 5, 414-428. Takahashi, T.; Kusaka, S.; Doi, T.; Sunazuka, T.; Omura, S. Angew. Chem., Int. Ed. 2003, 42, 5230-5234.
    • (2003) Org. Lett. , vol.5 , pp. 1159-1162
    • Tanaka, H.1    Ohno, H.2    Kawamura, K.3    Ohtake, A.4    Nagase, H.5    Takahashi, T.6
  • 10
    • 0242543873 scopus 로고    scopus 로고
    • For our reports of the combinatorial synthesis of small-molecule libraries based on the structure of biologically active natural products, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716-3722. (c) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (d) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (e) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 1159-1162. (f) Tanaka, H.; Moriwaki, M.; Takahashi, M. Org. Lett. 2003, 5, 3807-3809. (g) Tanaka, H.; Amaya, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 3053-3057. (h) Takahashi, T.; Nagamiya, H.; Doi, T.; Peter, G.; Griffiths, P. G.; Bray, A. M. J. Comb. Chem. 2003, 5, 414-428. Takahashi, T.; Kusaka, S.; Doi, T.; Sunazuka, T.; Omura, S. Angew. Chem., Int. Ed. 2003, 42, 5230-5234.
    • (2003) Org. Lett. , vol.5 , pp. 3807-3809
    • Tanaka, H.1    Moriwaki, M.2    Takahashi, M.3
  • 11
    • 0037424734 scopus 로고    scopus 로고
    • For our reports of the combinatorial synthesis of small-molecule libraries based on the structure of biologically active natural products, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716-3722. (c) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (d) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (e) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 1159-1162. (f) Tanaka, H.; Moriwaki, M.; Takahashi, M. Org. Lett. 2003, 5, 3807-3809. (g) Tanaka, H.; Amaya, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 3053-3057. (h) Takahashi, T.; Nagamiya, H.; Doi, T.; Peter, G.; Griffiths, P. G.; Bray, A. M. J. Comb. Chem. 2003, 5, 414-428. Takahashi, T.; Kusaka, S.; Doi, T.; Sunazuka, T.; Omura, S. Angew. Chem., Int. Ed. 2003, 42, 5230-5234.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 3053-3057
    • Tanaka, H.1    Amaya, T.2    Takahashi, T.3
  • 12
    • 0141675075 scopus 로고    scopus 로고
    • For our reports of the combinatorial synthesis of small-molecule libraries based on the structure of biologically active natural products, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716-3722. (c) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (d) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (e) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 1159-1162. (f) Tanaka, H.; Moriwaki, M.; Takahashi, M. Org. Lett. 2003, 5, 3807-3809. (g) Tanaka, H.; Amaya, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 3053-3057. (h) Takahashi, T.; Nagamiya, H.; Doi, T.; Peter, G.; Griffiths, P. G.; Bray, A. M. J. Comb. Chem. 2003, 5, 414-428. Takahashi, T.; Kusaka, S.; Doi, T.; Sunazuka, T.; Omura, S. Angew. Chem., Int. Ed. 2003, 42, 5230-5234.
    • (2003) J. Comb. Chem. , vol.5 , pp. 414-428
    • Takahashi, T.1    Nagamiya, H.2    Doi, T.3    Peter, G.4    Griffiths, P.G.5    Bray, A.M.6
  • 13
    • 0242636003 scopus 로고    scopus 로고
    • For our reports of the combinatorial synthesis of small-molecule libraries based on the structure of biologically active natural products, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716-3722. (c) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (d) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (e) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 1159-1162. (f) Tanaka, H.; Moriwaki, M.; Takahashi, M. Org. Lett. 2003, 5, 3807-3809. (g) Tanaka, H.; Amaya, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 3053-3057. (h) Takahashi, T.; Nagamiya, H.; Doi, T.; Peter, G.; Griffiths, P. G.; Bray, A. M. J. Comb. Chem. 2003, 5, 414-428. (i) Takahashi, T.; Kusaka, S.; Doi, T.; Sunazuka, T.; Omura, S. Angew. Chem., Int. Ed. 2003, 42, 5230-5234.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5230-5234
    • Takahashi, T.1    Kusaka, S.2    Doi, T.3    Sunazuka, T.4    Omura, S.5
  • 41
    • 2342453666 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of the corresponding MTPA ester of the secondary alcohol to be >98%ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.