메뉴 건너뛰기




Volumn 43, Issue 10, 2004, Pages 1196-1216

Synthesis and properties of allenic natural products and pharmaceuticals

Author keywords

Allenes; Cumulenes; Natural products; Pharmaceuticals; Stereoselective; Synthesis

Indexed keywords

AMINO ACIDS; DERIVATIVES; ENZYME INHIBITION; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL);

EID: 4544276732     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200300628     Document Type: Review
Times cited : (757)

References (301)
  • 2
    • 0003623760 scopus 로고
    • (Ed.: S. R. Landor), Academic Press, London
    • b) The Chemistry of the Allenes (Ed.: S. R. Landor), Academic Press, London, 1982;
    • (1982) The Chemistry of the Allenes
  • 4
    • 0001302333 scopus 로고
    • (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart
    • d) C. J. Elsevier in Methods of Organic Chemistry (Houben-Weyl), Vol. E21a (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1955, pp. 537-566;
    • (1955) Methods of Organic Chemistry (Houben-Weyl), Vol. E21a , pp. 537-566
    • Elsevier, C.J.1
  • 5
    • 4544320494 scopus 로고    scopus 로고
    • (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim
    • e) Modern Allene Chemistry (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004.
    • (2004) Modern Allene Chemistry
  • 9
    • 0003623760 scopus 로고
    • (Ed.: S. R. Landor), Academic Press, London
    • a) "Naturally Occurring Allenes": S. R. Landor in The Chemistry of the Allenes (Ed.: S. R. Landor), Academic Press, London, 1982, pp. 679-707;
    • (1982) The Chemistry of the Allenes , pp. 679-707
    • Landor, S.R.1
  • 10
    • 4544315570 scopus 로고
    • Biologically active allenes
    • (Ed.: S. R. Landor), Academic Press, London
    • b) A. Claesson, Biologically Active Allenes in The Chemistry of the Allenes (Ed.: S. R. Landor), Academic Press, London, 1982, pp. 709-733;
    • (1982) The Chemistry of the Allenes , pp. 709-733
    • Claesson, A.1
  • 17
    • 4544310910 scopus 로고    scopus 로고
    • note
    • Interestingly, this correction has not been included in the well-known monograph by Schuster and Coppola;[1c] here, pyrothrolone is mentioned on p. 1 as the first naturally occurring allene!
  • 22
    • 4544358574 scopus 로고    scopus 로고
    • note
    • A literature survey carried out in August 2003 in the Beilstein database BS0302PR (allene with maximum degrees of freedom in the structure editor, inp = * in the fact editor) gave 194 hits. After taking into account redundant or wrong entries and several compounds not included in this database, 146 allenic natural products (38 linear allenes, 46 allenic carotinoids and terpenoids, 33 bromoallenes, 29 other allenes) and 4 natural products with cumulene structure remained.
  • 23
    • 0004246896 scopus 로고    scopus 로고
    • (Ed.: N. Krause), Wiley-VCH, Weinheim
    • a) "Copper-Mediated Addition and Substitution Reactions of Extended Multiple Bond Systems": N. Krause, A. Hoffmann-Röder in Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 145-166;
    • (2002) Modern Organocopper Chemistry , pp. 145-166
    • Krause, N.1    Hoffmann-Röder, A.2
  • 26
    • 0037119342 scopus 로고    scopus 로고
    • c) A. Hoffmann-Röder, N. Krause, Angew. Chem. 2002, 114, 3057-3059; Angew. Chem. Int. Ed. 2002, 41, 2933-2935.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2933-2935
  • 28
    • 0012257381 scopus 로고
    • b) W. D. Celmer, I. A. Solomons, J. Am. Chem. Soc. 1952, 74, 1870-1871; W. D. Celmer, I. A. Solomons, J. Am. Chem. Soc. 1952, 74, 2245-2248; W. D. Celmer, I. A. Solomons, J. Am. Chem. Soc. 1952, 74, 3838-3842.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 1870-1871
    • Celmer, W.D.1    Solomons, I.A.2
  • 29
    • 0141661735 scopus 로고
    • b) W. D. Celmer, I. A. Solomons, J. Am. Chem. Soc. 1952, 74, 1870-1871; W. D. Celmer, I. A. Solomons, J. Am. Chem. Soc. 1952, 74, 2245-2248; W. D. Celmer, I. A. Solomons, J. Am. Chem. Soc. 1952, 74, 3838-3842.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 2245-2248
    • Celmer, W.D.1    Solomons, I.A.2
  • 30
    • 1242295922 scopus 로고
    • b) W. D. Celmer, I. A. Solomons, J. Am. Chem. Soc. 1952, 74, 1870-1871; W. D. Celmer, I. A. Solomons, J. Am. Chem. Soc. 1952, 74, 2245-2248; W. D. Celmer, I. A. Solomons, J. Am. Chem. Soc. 1952, 74, 3838-3842.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 3838-3842
    • Celmer, W.D.1    Solomons, I.A.2
  • 31
    • 0344748750 scopus 로고
    • a) G. Bendz, Arkiv. Kemi 1959, 14, 305-321; G. Bendz, Arkiv. Kemi 1959, 14, 475-481;
    • (1959) Arkiv. Kemi , vol.14 , pp. 305-321
    • Bendz, G.1
  • 32
    • 4544272823 scopus 로고
    • a) G. Bendz, Arkiv. Kemi 1959, 14, 305-321; G. Bendz, Arkiv. Kemi 1959, 14, 475-481;
    • (1959) Arkiv. Kemi , vol.14 , pp. 475-481
    • Bendz, G.1
  • 51
    • 0001334338 scopus 로고    scopus 로고
    • c) N. Krause, A. Gerold, Angew. Chem. 1997, 109, 194-213; Angew. Chem. Int. Ed. Engl. 1997, 36, 186-204.
    • (1997) Angew. Chem. , vol.109 , pp. 194-213
    • Krause, N.1    Gerold, A.2
  • 52
    • 0030902124 scopus 로고    scopus 로고
    • c) N. Krause, A. Gerold, Angew. Chem. 1997, 109, 194-213; Angew. Chem. Int. Ed. Engl. 1997, 36, 186-204.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 186-204
  • 81
    • 84987492232 scopus 로고
    • and references therein
    • Isolation and structure: A. Baumeler, C. H. Eugster, Helv. Chim. Acta 1992, 75, 773-790, and references therein.
    • (1992) Helv. Chim. Acta , vol.75 , pp. 773-790
    • Baumeler, A.1    Eugster, C.H.2
  • 122
    • 0037087785 scopus 로고    scopus 로고
    • N. Furuichi, H. Hara, T. Osaki, H. Mori, S. Katsumura, Angew. Chem. 2002, 114, 1065-1068; Angew. Chem. Int. Ed. 2002, 41, 1023-1026.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1023-1026
  • 128
  • 146
    • 4544351096 scopus 로고    scopus 로고
    • ref. [65c]
    • d) ref. [65c].
  • 163
    • 0345476898 scopus 로고    scopus 로고
    • P. A. Evans, V. S. Murthy, J. D. Roseman, A. L. Rheingold, Angew. Chem. 1999, 111, 3370-3372; Angew. Chem. Int. Ed. 1999, 38, 3175-3177.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3175-3177
  • 171
    • 4544297481 scopus 로고
    • d) allenic steroid: N. Theobald, J. N. Shoolery, C. Djerassi, T. R. Erdman, P. J. Scheuer, J. Am. Chem. Soc. 1978, 100, 5574-5575 (isolation); M. Morisaki, N. Awata, Y. Fujimoto, N. Ikekawa, J. Chem. Soc. Perkin Trans. 1 1975, 362-363 (synthesis); Y. Fujimoto, M. Morisaki, N. Ikekawa, J. Chem. Soc. Perkin Trans. 1 1975, 2302-2307 (synthesis).
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 5574-5575
    • Theobald, N.1    Shoolery, J.N.2    Djerassi, C.3    Erdman, T.R.4    Scheuer, P.J.5
  • 172
    • 34748844038 scopus 로고
    • d) allenic steroid: N. Theobald, J. N. Shoolery, C. Djerassi, T. R. Erdman, P. J. Scheuer, J. Am. Chem. Soc. 1978, 100, 5574-5575 (isolation); M. Morisaki, N. Awata, Y. Fujimoto, N. Ikekawa, J. Chem. Soc. Perkin Trans. 1 1975, 362-363 (synthesis); Y. Fujimoto, M. Morisaki, N. Ikekawa, J. Chem. Soc. Perkin Trans. 1 1975, 2302-2307 (synthesis).
    • (1975) J. Chem. Soc. Perkin Trans. 1 , pp. 362-363
    • Morisaki, M.1    Awata, N.2    Fujimoto, Y.3    Ikekawa, N.4
  • 173
    • 37049135906 scopus 로고
    • d) allenic steroid: N. Theobald, J. N. Shoolery, C. Djerassi, T. R. Erdman, P. J. Scheuer, J. Am. Chem. Soc. 1978, 100, 5574-5575 (isolation); M. Morisaki, N. Awata, Y. Fujimoto, N. Ikekawa, J. Chem. Soc. Perkin Trans. 1 1975, 362-363 (synthesis); Y. Fujimoto, M. Morisaki, N. Ikekawa, J. Chem. Soc. Perkin Trans. 1 1975, 2302-2307 (synthesis).
    • (1975) J. Chem. Soc. Perkin Trans. 1 , pp. 2302-2307
    • Fujimoto, Y.1    Morisaki, M.2    Ikekawa, N.3
  • 189
    • 4544320111 scopus 로고    scopus 로고
    • J. Takashima, S. Asano, A. Ohsaki, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 2000, 487-492 [Chem. Abstr. 2001, 135, 104 986].
    • (2001) Chem. Abstr. , vol.135
  • 198
    • 4544339028 scopus 로고    scopus 로고
    • note
    • The structures of five additional endocyclic allenes found in the Beilstein database (e.g., an 11-membered ring system[97e]) are probably incorrect.
  • 202
    • 4544294284 scopus 로고
    • c) F. Bohlmann, C. Zdero, Tetrahedron Lett. 1970, 2465-2466; F. Bohlmann, C. Zdero, Chem. Ber. 1971, 104, 1329-1331.
    • (1971) Chem. Ber. , vol.104 , pp. 1329-1331
    • Bohlmann, F.1    Zdero, C.2
  • 204
    • 0019628629 scopus 로고
    • 14C-marked mevanolate by the alga Amphidinium carterae are not in accordance with the formation of the exocyclic allene from an alkyne: I. E. Swift, B. V. Milborrow, Biochem. J. 1981, 199, 69-74.
    • (1981) Biochem. J. , vol.199 , pp. 69-74
    • Swift, I.E.1    Milborrow, B.V.2
  • 205
  • 229
  • 251
    • 0024520577 scopus 로고
    • The activity as enzyme inhibitors of halogenated amino acids (which can be transformed into allenic amino acids by enzymatic dehydrohalogenation) may be caused by the same mechanism: a) N. Esaki, H. Takada, M. Moriguchi, S. Hatanaka, H. Tanaka, K. Soda, Biochemistry 1989, 28, 2111-2116;
    • (1989) Biochemistry , vol.28 , pp. 2111-2116
    • Esaki, N.1    Takada, H.2    Moriguchi, M.3    Hatanaka, S.4    Tanaka, H.5    Soda, K.6
  • 256
    • 84989538019 scopus 로고
    • a) B. Kübel, G. Höfle, W. Steglich, Angew. Chem. 1975, 87, 64-66; Angew. Chem. Int. Ed. Engl. 1975, 14, 58-60;
    • (1975) Angew. Chem. Int. Ed. Engl. , vol.14 , pp. 58-60
  • 258
    • 84980186277 scopus 로고
    • b) N. Engel, B. Kübel, W. Steglich, Angew. Chem. 1977, 89, 408-410; Angew. Chem. Int. Ed. Engl. 1977, 16, 394-396;
    • (1977) Angew. Chem. Int. Ed. Engl. , vol.16 , pp. 394-396
  • 266
    • 0027393930 scopus 로고
    • Enzyme-catalyzed kinetic deracemization of unsaturated GABA derivatives: A. L. Margolin, Tetrahedron Lett. 1993, 34, 1239-1242.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1239-1242
    • Margolin, A.L.1
  • 268
    • 0029670555 scopus 로고    scopus 로고
    • Compare: a) formation of γ-allenyl-GABA from 4-amino-5-fluorohex-5- enoic acid by enzymatic dehydrohalogenation: R. B. Silverman, K. A. Bichler, A. J. Leon, J. Am. Chem. Soc. 1996, 118, 1241-1252;
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1241-1252
    • Silverman, R.B.1    Bichler, K.A.2    Leon, A.J.3
  • 296
    • 0000070605 scopus 로고
    • Reviews: a) K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453-1481; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416;
    • (1991) Angew. Chem. , vol.103 , pp. 1453-1481
    • Nicolaou, K.C.1    Dai, W.-M.2
  • 297
    • 0026045597 scopus 로고
    • Reviews: a) K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453-1481; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416;
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 1387-1416
  • 300
    • 0000770422 scopus 로고    scopus 로고
    • d) K. K. Wang, Chem. Rev. 1996, 96, 207-222;
    • (1996) Chem. Rev. , vol.96 , pp. 207-222
    • Wang, K.K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.