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Volumn 65, Issue 12, 2001, Pages 2630-2637

Synthesis of southern (C1′-C11′) and eastern (C8-C18) fragments of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger

Author keywords

Aerial mycelium; Antibiotic; Iodoetherification; Pamamycin; Synthesis

Indexed keywords

STREPTOMYCES; STREPTOMYCES ALBONIGER;

EID: 0035752439     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.65.2630     Document Type: Article
Times cited : (11)

References (27)
  • 1
    • 0018562172 scopus 로고
    • Pamamycin: A new antibiotic and stimulator of aerial mycelia formation
    • a) McCann, P. A. and Pogell, B. M., Pamamycin: a new antibiotic and stimulator of aerial mycelia formation. J. Antibiot., 32, 673-678 (1979).
    • (1979) J. Antibiot. , vol.32 , pp. 673-678
    • McCann, P.A.1    Pogell, B.M.2
  • 2
    • 0025829142 scopus 로고
    • The structure of four new pamamycin homologs isolated from Streptomyces alboniger
    • b) Natsume, M., Yasui, K., Kondo, S., and Marumo, S., The structure of four new pamamycin homologs isolated from Streptomyces alboniger. Tetrahedron Lett., 32, 3087-3090 (1991).
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3087-3090
    • Natsume, M.1    Yasui, K.2    Kondo, S.3    Marumo, S.4
  • 3
    • 0028785205 scopus 로고
    • Structure-activity relationship of pamamycins: Effects of alkyl substituents
    • c) Natsume, M., Tazawa, J., Yagi, K., Abe, H., Kondo, S., and Marumo, S., Structure-activity relationship of pamamycins: effects of alkyl substituents. J. Antibiot., 48, 1159-1164 (1995).
    • (1995) J. Antibiot. , vol.48 , pp. 1159-1164
    • Natsume, M.1    Tazawa, J.2    Yagi, K.3    Abe, H.4    Kondo, S.5    Marumo, S.6
  • 4
    • 19044397794 scopus 로고    scopus 로고
    • Study on bio-organic chemistry of aerial mycelium-differentiation in actinomycetes
    • d) Recent review: Natsume, M., Study on bio-organic chemistry of aerial mycelium-differentiation in actinomycetes. Nippon Nogei Kagaku Kaishi (in Japanese), 72, 19-25 (1998).
    • (1998) Nippon Nogei Kagaku Kaishi (in Japanese) , vol.72 , pp. 19-25
    • Natsume, M.1
  • 5
    • 0023712615 scopus 로고
    • Isolation, physico-chemical properties and biological activity of pamamycin-607, an aerial mycelium-inducing substance from Streptomyces alboniger
    • a) Kondo, S., Yasui, K., Natsume, M., Katayama, M., and Marumo, S., Isolation, physico-chemical properties and biological activity of pamamycin-607, an aerial mycelium-inducing substance from Streptomyces alboniger. J. Antibiot., 41, 1196-1204 (1988).
    • (1988) J. Antibiot. , vol.41 , pp. 1196-1204
    • Kondo, S.1    Yasui, K.2    Natsume, M.3    Katayama, M.4    Marumo, S.5
  • 6
    • 0023639445 scopus 로고
    • Structure of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger
    • b) Kondo, S., Yasui, K., Katayama, M., Marumo, S., Kondo, S., and Hattori, H., Structure of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger. Tetrahedron Lett., 28, 5861-5864 (1987).
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5861-5864
    • Kondo, S.1    Yasui, K.2    Katayama, M.3    Marumo, S.4    Kondo, S.5    Hattori, H.6
  • 7
    • 0024827198 scopus 로고
    • The absolute stereochemistry of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger
    • c) Natsume, M., Kondo, S., and Marumo, S., The absolute stereochemistry of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger. J. Chem. Soc., Chem. Commun., 1911-1913 (1989).
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 1911-1913
    • Natsume, M.1    Kondo, S.2    Marumo, S.3
  • 8
    • 0028910945 scopus 로고
    • Synthesis of the C1-C14 subunit of macrodiolide antibiotics pamamycin-607 and pamamycin-635B
    • Walkup, R. D. and Kim, Y. S., Synthesis of the C1-C14 subunit of macrodiolide antibiotics pamamycin-607 and pamamycin-635B. Tetrahedron Lett., 36, 3091-3094 (1995).
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3091-3094
    • Walkup, R.D.1    Kim, Y.S.2
  • 9
    • 0029997910 scopus 로고    scopus 로고
    • The total synthesis of pamamycin-607. 1. Synthesis of a C1′-C11′ synthon
    • Mavropoulos, I. and Perlmutter, P., The total synthesis of pamamycin-607. 1. Synthesis of a C1′-C11′ synthon. Tetrahedron Lett., 37, 3751-3754 (1996).
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3751-3754
    • Mavropoulos, I.1    Perlmutter, P.2
  • 10
    • 0031566708 scopus 로고    scopus 로고
    • A novel and efficient stereoselective synthesis of the southern fragment of pamamycin-607
    • Mandville, G., Girald, C., and Bloch, R., A novel and efficient stereoselective synthesis of the southern fragment of pamamycin-607. Tetrahedron: Asymmetry, 8, 3665-3673 (1997).
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 3665-3673
    • Mandville, G.1    Girald, C.2    Bloch, R.3
  • 12
    • 0034620943 scopus 로고    scopus 로고
    • Diastereodivergent synthesis of the C8-C18 precursor and C1′-C11′ subunit of pamamycin-607 induced by a chiral sulfoxide group
    • Solladie, G., Salom-Roig, X. J., and Hanquet, G., Diastereodivergent synthesis of the C8-C18 precursor and C1′-C11′ subunit of pamamycin-607 induced by a chiral sulfoxide group. Tetrahedron Lett., 41, 2737-2740 (2000).
    • (2000) Tetrahedron Lett. , vol.41 , pp. 2737-2740
    • Solladie, G.1    Salom-Roig, X.J.2    Hanquet, G.3
  • 13
    • 0032829190 scopus 로고    scopus 로고
    • Towards the total synthesis of pamamycin-607: Preparation of the eastern fragment, (C8-C18 fragment)
    • Mandville, G. and Bloch, R., Towards the total synthesis of pamamycin-607: Preparation of the eastern fragment, (C8-C18 fragment). Eur. J. Org. Chem., 2303-2307 (1999).
    • (1999) Eur. J. Org. Chem. , pp. 2303-2307
    • Mandville, G.1    Bloch, R.2
  • 14
    • 0034700859 scopus 로고    scopus 로고
    • Stereoselective synthesis towards the C8-C18 subunit of pamamycin-607 induced by a chiral sulfoxide group
    • Solladié, G., Salom-Roig, X. J., and Hanquet, G., Stereoselective synthesis towards the C8-C18 subunit of pamamycin-607 induced by a chiral sulfoxide group. Tetrahedron Lett., 41, 551-554 (2000).
    • (2000) Tetrahedron Lett. , vol.41 , pp. 551-554
    • Solladié, G.1    Salom-Roig, X.J.2    Hanquet, G.3
  • 15
    • 17644435930 scopus 로고    scopus 로고
    • A sultone approach to the C(1)-C(18) moiety of pamamycin-607
    • Bernsmann, H., Frölich, R., and Metz, P., A sultone approach to the C(1)-C(18) moiety of pamamycin-607. Tetrahedron Lett., 41, 4347-4351 (2000).
    • (2000) Tetrahedron Lett. , vol.41 , pp. 4347-4351
    • Bernsmann, H.1    Frölich, R.2    Metz, P.3
  • 16
    • 0034734651 scopus 로고    scopus 로고
    • Enantioselective synthesis of the large fragment of pamamycin-607
    • Bernsmann, H., Gruner, M., and Metz, P., Enantioselective synthesis of the large fragment of pamamycin-607. Tetrahedron Lett., 41, 7629-7633 (2000).
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7629-7633
    • Bernsmann, H.1    Gruner, M.2    Metz, P.3
  • 17
    • 0034556691 scopus 로고    scopus 로고
    • Synthesis of the southern fragment of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger
    • Furuya, Y., Kiyota, H., and Oritani, T., Synthesis of the southern fragment of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger. Heterocycl. Commun., 6, 427-430 (2000).
    • (2000) Heterocycl. Commun. , vol.6 , pp. 427-430
    • Furuya, Y.1    Kiyota, H.2    Oritani, T.3
  • 18
    • 0942275241 scopus 로고    scopus 로고
    • Synthesis of (±)-homononactic acid by using cis-selective iodoetherification
    • Abe, M., Kiyota, H., Adachi, M., and Oritani, T., Synthesis of (±)-homononactic acid by using cis-selective iodoetherification. Synlett, 777-778 (1996).
    • (1996) Synlett , pp. 777-778
    • Abe, M.1    Kiyota, H.2    Adachi, M.3    Oritani, T.4
  • 19
    • 0001303122 scopus 로고    scopus 로고
    • Synthesis of (+)-homononactic acid via iodoetherification
    • Kiyota, H., Abe, M., Ono, Y., and Oritani, T., Synthesis of (+)-homononactic acid via iodoetherification. Synlett, 1093-1095 (1997).
    • (1997) Synlett , pp. 1093-1095
    • Kiyota, H.1    Abe, M.2    Ono, Y.3    Oritani, T.4
  • 20
    • 0034252046 scopus 로고    scopus 로고
    • Synthesis of (±)-methyl bishomononactate, a monomeric component of polynactin antibiotics
    • Hanadate, T., Kiyota, H., and Oritani, T., Synthesis of (±)-methyl bishomononactate, a monomeric component of polynactin antibiotics. Biosci. Biotechnol. Biochem., 64, 1671-1674 (2000).
    • (2000) Biosci. Biotechnol. Biochem. , vol.64 , pp. 1671-1674
    • Hanadate, T.1    Kiyota, H.2    Oritani, T.3
  • 21
    • 0035460365 scopus 로고    scopus 로고
    • Synthesis of macrotetrolide a, a designed polynactin analog composed of (+)- and (-)-bishomononactic acids
    • Idem., Synthesis of macrotetrolide a, a designed polynactin analog composed of (+)- and (-)-bishomononactic acids. Biosci. Biotechnol. Biochem., 65, 2118-2120 (2001).
    • (2001) Biosci. Biotechnol. Biochem. , vol.65 , pp. 2118-2120
    • Hanadate, T.1    Kiyota, H.2    Oritani, T.3
  • 22
    • 33845555768 scopus 로고
    • Stereocontrolled synthesis of cis-2.5-disubstituted tetrahydrofurans and cis- and trans-linalyl oxides
    • a) Rychnovsky, S. D. and Bartlett, P. A., Stereocontrolled synthesis of cis-2.5-disubstituted tetrahydrofurans and cis- and trans-linalyl oxides. J. Am. Chem. Soc., 103, 3963-3964 (1981).
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3963-3964
    • Rychnovsky, S.D.1    Bartlett, P.A.2
  • 23
    • 0026562325 scopus 로고
    • Iodocyclization of olefinic t-butyl ethers: An easy stereocontrolled synthesis of cis-substituted tetrahydrofurans
    • b) Marek, I., Lefrançois, J.-M., and Normant, J.-F., Iodocyclization of olefinic t-butyl ethers: an easy stereocontrolled synthesis of cis-substituted tetrahydrofurans. Tetrahedron Lett., 33, 1747-1748 (1992).
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1747-1748
    • Marek, I.1    Lefrançois, J.-M.2    Normant, J.-F.3
  • 24
    • 0012016624 scopus 로고
    • Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates
    • Evans, D. A., Bartroli, J., and Shin, T. L., Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates. J. Am. Chem. Soc., 103, 2127-2129 (1981).
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 2127-2129
    • Evans, D.A.1    Bartroli, J.2    Shin, T.L.3
  • 25
    • 0000609486 scopus 로고
    • Synthesis of (R)-1-benzyloxy-3-butene-2-ol a potential chiral synthon from l-(+)-tartaric acid: Its applications in natural product synthesis
    • Rama Rao, A. V., Reddy, E. R., Joshi, B. V., and Yadav, J. S., Synthesis of (R)-1-benzyloxy-3-butene-2-ol a potential chiral synthon from L-(+)-tartaric acid: its applications in natural product synthesis. Tetrahedron Lett., 28, 6497-6500 (1987).
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6497-6500
    • Rama Rao, A.V.1    Reddy, E.R.2    Joshi, B.V.3    Yadav, J.S.4
  • 26
    • 0028934744 scopus 로고
    • Total synthesis of the polyene macrolide antibiotic roxaticin. 1. Synthesis of the polyol fragment of roxaticin using a four-carbon chain extension strategy
    • 3), Mori, Y., Asai, M., Okumura, A., and Furukawa, H., Total synthesis of the polyene macrolide antibiotic roxaticin. 1. Synthesis of the polyol fragment of roxaticin using a four-carbon chain extension strategy. Tetrahedron, 51, 5299-5314 (1995).
    • (1995) Tetrahedron , vol.51 , pp. 5299-5314
    • Mori, Y.1    Asai, M.2    Okumura, A.3    Furukawa, H.4
  • 27
    • 0000830549 scopus 로고
    • Di-astereoselective aldol condensation using a chiral oxazolidinone auxiliary(2s* ,3s*)-3-hydroxy-3-phenyl-2-methylpropanoic acid
    • D + 92.9° (c = 1.01, EtOH), Gage, J. R. and Evans, D. A., Di-astereoselective aldol condensation using a chiral oxazolidinone auxiliary(2S* ,3S*)-3-hydroxy-3-phenyl-2-methylpropanoic acid. Org. Synth., Coll. Vol. VIII, 339-343 (1993).
    • (1993) Org. Synth., Coll. Vol. VIII , vol.8 , pp. 339-343
    • Gage, J.R.1    Evans, D.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.