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Volumn 8, Issue 18, 2002, Pages 4255-4264

Lipase-catalyzed domino kinetic resolution/intramolecular Diels-Alder-reaction: One-pot synthesis of optically active 7-oxabicyclo[2.2.1]heptenes from furfuryl alcohols and β-substituted acrylic acids

Author keywords

Asymmetric synthesis; Cycloadditions; Domino reactions; Hydrolases; Kinetic resolution

Indexed keywords

ALCOHOLS; CARBON; CATALYSIS; DERIVATIVES; ESTERS; ORGANIC ACIDS;

EID: 0037120158     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20020916)8:18<4255::AID-CHEM4255>3.0.CO;2-6     Document Type: Article
Times cited : (43)

References (75)
  • 2
    • 0034608087 scopus 로고    scopus 로고
    • b) F. Theil, Tetrahedron 2000, 56, 2905-2919;
    • (2000) Tetrahedron , vol.56 , pp. 2905-2919
    • Theil, F.1
  • 7
    • 0036003112 scopus 로고    scopus 로고
    • Recent papers, see: T. Itoh, E. Akasaki, Y. Nishimura, Chem. Lett. 2002, 154-155; S. Park, R. J. Kazlauskas. J. Org. Chem. 2001, 66, 8395-8401.
    • (2002) Chem. Lett. , pp. 154-155
    • Itoh, T.1    Akasaki, E.2    Nishimura, Y.3
  • 8
    • 0035861716 scopus 로고    scopus 로고
    • Recent papers, see: T. Itoh, E. Akasaki, Y. Nishimura, Chem. Lett. 2002, 154-155; S. Park, R. J. Kazlauskas. J. Org. Chem. 2001, 66, 8395-8401.
    • (2001) J. Org. Chem. , vol.66 , pp. 8395-8401
    • Park, S.1    Kazlauskas, R.J.2
  • 15
    • 57249083957 scopus 로고    scopus 로고
    • For a review on enzyme-initiated domino reactions, see: S. F. Mayer, W. Kroutil, K. Faber, Chem. Soc. Rev. 2001, 30, 332-339; for reviews on the chemical domino reactions, see: L. F. Tietze, Chem. Rev. 1996, 96, 115-136; L. E Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. 1993, 32, 131-163.
    • (2001) Chem. Soc. Rev. , vol.30 , pp. 332-339
    • Mayer, S.F.1    Kroutil, W.2    Faber, K.3
  • 16
    • 7044235263 scopus 로고    scopus 로고
    • For a review on enzyme-initiated domino reactions, see: S. F. Mayer, W. Kroutil, K. Faber, Chem. Soc. Rev. 2001, 30, 332-339; for reviews on the chemical domino reactions, see: L. F. Tietze, Chem. Rev. 1996, 96, 115-136; L. E Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. 1993, 32, 131-163.
    • (1996) Chem. Rev. , vol.96 , pp. 115-136
    • Tietze, L.F.1
  • 17
    • 57249083957 scopus 로고    scopus 로고
    • For a review on enzyme-initiated domino reactions, see: S. F. Mayer, W. Kroutil, K. Faber, Chem. Soc. Rev. 2001, 30, 332-339; for reviews on the chemical domino reactions, see: L. F. Tietze, Chem. Rev. 1996, 96, 115-136; L. E Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. 1993, 32, 131-163.
    • (1993) Angew. Chem. , vol.105 , pp. 137-170
    • Tietze, L.E.1    Beifuss, U.2
  • 18
    • 33750173220 scopus 로고
    • For a review on enzyme-initiated domino reactions, see: S. F. Mayer, W. Kroutil, K. Faber, Chem. Soc. Rev. 2001, 30, 332-339; for reviews on the chemical domino reactions, see: L. F. Tietze, Chem. Rev. 1996, 96, 115-136; L. E Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. 1993, 32, 131-163.
    • (1993) Angew. Chem. Int. Ed. , vol.32 , pp. 131-163
  • 26
    • 0025733902 scopus 로고
    • [8c] see: a) B. Berger, K. Faber, J. Chem. Soc. Chem. Commun. 1991, 1198-1200; b) H. K. Weber, J. Zuegg, K. Faber, J. Pleiss, J. Mol. Catal. B 1997, 3, 131-138; c) H.-E. Högberg, M. Lindmark, D. Isaksson, K. Sjödin, M. C. R. Franssen, H. Jongejan, J. B. P. A. Wijnberg, A. de Groot, Tetrahedron Lett. 2000, 41, 3193-3196.
    • (1991) J. Chem. Soc. Chem. Commun. , pp. 1198-1200
    • Berger, B.1    Faber, K.2
  • 27
    • 0342617775 scopus 로고    scopus 로고
    • [8c] see: a) B. Berger, K. Faber, J. Chem. Soc. Chem. Commun. 1991, 1198-1200; b) H. K. Weber, J. Zuegg, K. Faber, J. Pleiss, J. Mol. Catal. B 1997, 3, 131-138; c) H.-E. Högberg, M. Lindmark, D. Isaksson, K. Sjödin, M. C. R. Franssen, H. Jongejan, J. B. P. A. Wijnberg, A. de Groot, Tetrahedron Lett. 2000, 41, 3193-3196.
    • (1997) J. Mol. Catal. B , vol.3 , pp. 131-138
    • Weber, H.K.1    Zuegg, J.2    Faber, K.3    Pleiss, J.4
  • 29
    • 37049074301 scopus 로고
    • 2, see: Y. Kita, H. Maeda, K. Omori, T. Okuno, Y. Tamura, J. Chem. Soc. Perkin Trans. 1 1993, 2999-3005; Y. Kita, Y. Takeda, M. Matsugi, K. Iio, K. Gotanda, K. Murata, S. Akai, Angew. Chem. 1997, 109, 1525-1527; Angew. Chem. Int. Ed. Engl. 1997, 36, 1529-1531.
    • (1993) J. Chem. Soc. Perkin Trans. 1 , pp. 2999-3005
    • Kita, Y.1    Maeda, H.2    Omori, K.3    Okuno, T.4    Tamura, Y.5
  • 30
    • 0030799835 scopus 로고    scopus 로고
    • 2, see: Y. Kita, H. Maeda, K. Omori, T. Okuno, Y. Tamura, J. Chem. Soc. Perkin Trans. 1 1993, 2999-3005; Y. Kita, Y. Takeda, M. Matsugi, K. Iio, K. Gotanda, K. Murata, S. Akai, Angew. Chem. 1997, 109, 1525-1527; Angew. Chem. Int. Ed. Engl. 1997, 36, 1529-1531.
    • (1997) Angew. Chem. , vol.109 , pp. 1525-1527
    • Kita, Y.1    Takeda, Y.2    Matsugi, M.3    Iio, K.4    Gotanda, K.5    Murata, K.6    Akai, S.7
  • 31
    • 0030799835 scopus 로고    scopus 로고
    • 2, see: Y. Kita, H. Maeda, K. Omori, T. Okuno, Y. Tamura, J. Chem. Soc. Perkin Trans. 1 1993, 2999-3005; Y. Kita, Y. Takeda, M. Matsugi, K. Iio, K. Gotanda, K. Murata, S. Akai, Angew. Chem. 1997, 109, 1525-1527; Angew. Chem. Int. Ed. Engl. 1997, 36, 1529-1531.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1529-1531
  • 33
    • 0033607764 scopus 로고    scopus 로고
    • For recent reviews, see: a) P. Vogel, J. Cossy, J. Plumet, O. Arjona, Tetrahedron 1999, 55, 13521-13642; b) C. O. Kappe, S. S. Murphree, A. Padwa, Tetrahedron 1997 53, 14179-14233; see also c) M. Murakami, H. Igawa, Chem. Commun. 2002, 390-391, and references therein.
    • (1999) Tetrahedron , vol.55 , pp. 13521-13642
    • Vogel, P.1    Cossy, J.2    Plumet, J.3    Arjona, O.4
  • 34
    • 0030845835 scopus 로고    scopus 로고
    • For recent reviews, see: a) P. Vogel, J. Cossy, J. Plumet, O. Arjona, Tetrahedron 1999, 55, 13521-13642; b) C. O. Kappe, S. S. Murphree, A. Padwa, Tetrahedron 1997 53, 14179-14233; see also c) M. Murakami, H. Igawa, Chem. Commun. 2002, 390-391, and references therein.
    • (1997) Tetrahedron , vol.53 , pp. 14179-14233
    • Kappe, C.O.1    Murphree, S.S.2    Padwa, A.3
  • 35
    • 0037148763 scopus 로고    scopus 로고
    • and references therein
    • For recent reviews, see: a) P. Vogel, J. Cossy, J. Plumet, O. Arjona, Tetrahedron 1999, 55, 13521-13642; b) C. O. Kappe, S. S. Murphree, A. Padwa, Tetrahedron 1997 53, 14179-14233; see also c) M. Murakami, H. Igawa, Chem. Commun. 2002, 390-391, and references therein.
    • (2002) Chem. Commun. , pp. 390-391
    • Murakami, M.1    Igawa, H.2
  • 39
    • 0000703343 scopus 로고
    • Sharpless asymmetric epoxidation of racemic 3, see: a) M. Kusakabe, Y. Kitano, Y. Kobayashi, F. Sato. J. Org. Chem. 1989, 54, 2085-2091; b) T. Kametani, M. Tsubuki, Y. Tatsuzaki, T. Honda, J. Chem. Soc. Perkin Trans. 1 1990, 639-646; enantioselective addition of diethyl zinc to furfural, see: c) M. Hayashi, T. Kaneko, N. Oguni, J. Chem. Soc. Perkin Trans. 1 1991, 25-28; d) I. Sato, T. Saito, D. Omiya, Y. Takizawa, K. Soai. Heterocycles 1999, 51, 2753-2758; enantioselective reduction of 2-acyfurans; see: e) R. Noyori, T Ohkuma, Angew. Chem. 2001, 113, 41-75; Angew. Chem. Int. Ed. 2001, 40, 40-73; f) T. Ohkuma, M. Koizumi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, 1749-1751.
    • (1989) J. Org. Chem. , vol.54 , pp. 2085-2091
    • Kusakabe, M.1    Kitano, Y.2    Kobayashi, Y.3    Sato, F.4
  • 40
    • 37049076417 scopus 로고
    • Sharpless asymmetric epoxidation of racemic 3, see: a) M. Kusakabe, Y. Kitano, Y. Kobayashi, F. Sato. J. Org. Chem. 1989, 54, 2085-2091; b) T. Kametani, M. Tsubuki, Y. Tatsuzaki, T. Honda, J. Chem. Soc. Perkin Trans. 1 1990, 639-646; enantioselective addition of diethyl zinc to furfural, see: c) M. Hayashi, T. Kaneko, N. Oguni, J. Chem. Soc. Perkin Trans. 1 1991, 25-28; d) I. Sato, T. Saito, D. Omiya, Y. Takizawa, K. Soai. Heterocycles 1999, 51, 2753-2758; enantioselective reduction of 2-acyfurans; see: e) R. Noyori, T Ohkuma, Angew. Chem. 2001, 113, 41-75; Angew. Chem. Int. Ed. 2001, 40, 40-73; f) T. Ohkuma, M. Koizumi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, 1749-1751.
    • (1990) J. Chem. Soc. Perkin Trans. 1 , pp. 639-646
    • Kametani, T.1    Tsubuki, M.2    Tatsuzaki, Y.3    Honda, T.4
  • 41
    • 0006381342 scopus 로고
    • Sharpless asymmetric epoxidation of racemic 3, see: a) M. Kusakabe, Y. Kitano, Y. Kobayashi, F. Sato. J. Org. Chem. 1989, 54, 2085-2091; b) T. Kametani, M. Tsubuki, Y. Tatsuzaki, T. Honda, J. Chem. Soc. Perkin Trans. 1 1990, 639-646; enantioselective addition of diethyl zinc to furfural, see: c) M. Hayashi, T. Kaneko, N. Oguni, J. Chem. Soc. Perkin Trans. 1 1991, 25-28; d) I. Sato, T. Saito, D. Omiya, Y. Takizawa, K. Soai. Heterocycles 1999, 51, 2753-2758; enantioselective reduction of 2-acyfurans; see: e) R. Noyori, T Ohkuma, Angew. Chem. 2001, 113, 41-75; Angew. Chem. Int. Ed. 2001, 40, 40-73; f) T. Ohkuma, M. Koizumi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, 1749-1751.
    • (1991) J. Chem. Soc. Perkin Trans. 1 , pp. 25-28
    • Hayashi, M.1    Kaneko, T.2    Oguni, N.3
  • 42
    • 0033230731 scopus 로고    scopus 로고
    • Sharpless asymmetric epoxidation of racemic 3, see: a) M. Kusakabe, Y. Kitano, Y. Kobayashi, F. Sato. J. Org. Chem. 1989, 54, 2085-2091; b) T. Kametani, M. Tsubuki, Y. Tatsuzaki, T. Honda, J. Chem. Soc. Perkin Trans. 1 1990, 639-646; enantioselective addition of diethyl zinc to furfural, see: c) M. Hayashi, T. Kaneko, N. Oguni, J. Chem. Soc. Perkin Trans. 1 1991, 25-28; d) I. Sato, T. Saito, D. Omiya, Y. Takizawa, K. Soai. Heterocycles 1999, 51, 2753-2758; enantioselective reduction of 2-acyfurans; see: e) R. Noyori, T Ohkuma, Angew. Chem. 2001, 113, 41-75; Angew. Chem. Int. Ed. 2001, 40, 40-73; f) T. Ohkuma, M. Koizumi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, 1749-1751.
    • (1999) Heterocycles , vol.51 , pp. 2753-2758
    • Sato, I.1    Saito, T.2    Omiya, D.3    Takizawa, Y.4    Soai, K.5
  • 43
    • 0001891348 scopus 로고    scopus 로고
    • Sharpless asymmetric epoxidation of racemic 3, see: a) M. Kusakabe, Y. Kitano, Y. Kobayashi, F. Sato. J. Org. Chem. 1989, 54, 2085-2091; b) T. Kametani, M. Tsubuki, Y. Tatsuzaki, T. Honda, J. Chem. Soc. Perkin Trans. 1 1990, 639-646; enantioselective addition of diethyl zinc to furfural, see: c) M. Hayashi, T. Kaneko, N. Oguni, J. Chem. Soc. Perkin Trans. 1 1991, 25-28; d) I. Sato, T. Saito, D. Omiya, Y. Takizawa, K. Soai. Heterocycles 1999, 51, 2753-2758; enantioselective reduction of 2-acyfurans; see: e) R. Noyori, T Ohkuma, Angew. Chem. 2001, 113, 41-75; Angew. Chem. Int. Ed. 2001, 40, 40-73; f) T. Ohkuma, M. Koizumi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, 1749-1751.
    • (2001) Angew. Chem. , vol.113 , pp. 41-75
    • Noyori, R.1    Ohkuma, T.2
  • 44
    • 37649026044 scopus 로고    scopus 로고
    • Sharpless asymmetric epoxidation of racemic 3, see: a) M. Kusakabe, Y. Kitano, Y. Kobayashi, F. Sato. J. Org. Chem. 1989, 54, 2085-2091; b) T. Kametani, M. Tsubuki, Y. Tatsuzaki, T. Honda, J. Chem. Soc. Perkin Trans. 1 1990, 639-646; enantioselective addition of diethyl zinc to furfural, see: c) M. Hayashi, T. Kaneko, N. Oguni, J. Chem. Soc. Perkin Trans. 1 1991, 25-28; d) I. Sato, T. Saito, D. Omiya, Y. Takizawa, K. Soai. Heterocycles 1999, 51, 2753-2758; enantioselective reduction of 2-acyfurans; see: e) R. Noyori, T Ohkuma, Angew. Chem. 2001, 113, 41-75; Angew. Chem. Int. Ed. 2001, 40, 40-73; f) T. Ohkuma, M. Koizumi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, 1749-1751.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 40-73
  • 45
    • 0001322847 scopus 로고    scopus 로고
    • Sharpless asymmetric epoxidation of racemic 3, see: a) M. Kusakabe, Y. Kitano, Y. Kobayashi, F. Sato. J. Org. Chem. 1989, 54, 2085-2091; b) T. Kametani, M. Tsubuki, Y. Tatsuzaki, T. Honda, J. Chem. Soc. Perkin Trans. 1 1990, 639-646; enantioselective addition of diethyl zinc to furfural, see: c) M. Hayashi, T. Kaneko, N. Oguni, J. Chem. Soc. Perkin Trans. 1 1991, 25-28; d) I. Sato, T. Saito, D. Omiya, Y. Takizawa, K. Soai. Heterocycles 1999, 51, 2753-2758; enantioselective reduction of 2-acyfurans; see: e) R. Noyori, T Ohkuma, Angew. Chem. 2001, 113, 41-75; Angew. Chem. Int. Ed. 2001, 40, 40-73; f) T. Ohkuma, M. Koizumi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, 1749-1751.
    • (2000) Org. Lett. , vol.2 , pp. 1749-1751
    • Ohkuma, T.1    Koizumi, M.2    Yoshida, M.3    Noyori, R.4
  • 46
    • 0026014628 scopus 로고
    • For kinetic resolution through the enzymatic transesterification of racemic 3 or the hydrolysis of the corresponding esters, see: a) A. J. M. Janssen, A. J. H. Klunder, B. Zwanenburg, Tetrahedron 1991, 47, 7645-7662; b) J. Kaminska, I. Górnicka, M. Sikora, J. Góra, Tetrahedron: Asymmetry 1996, 7, 907-910.
    • (1991) Tetrahedron , vol.47 , pp. 7645-7662
    • Janssen, A.J.M.1    Klunder, A.J.H.2    Zwanenburg, B.3
  • 47
    • 0343150944 scopus 로고    scopus 로고
    • For kinetic resolution through the enzymatic transesterification of racemic 3 or the hydrolysis of the corresponding esters, see: a) A. J. M. Janssen, A. J. H. Klunder, B. Zwanenburg, Tetrahedron 1991, 47, 7645-7662; b) J. Kaminska, I. Górnicka, M. Sikora, J. Góra, Tetrahedron: Asymmetry 1996, 7, 907-910.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 907-910
    • Kaminska, J.1    Górnicka, I.2    Sikora, M.3    Góra, J.4
  • 49
    • 0000973754 scopus 로고
    • During the intramolecular Diels-Alder reaction of furans, the equilibrium of the cycloadducts and their precursors has often been observed, see: a) C. Rogers, B. A. Keay, Can. J. Chem. 1993, 71, 611-622; b) N. Iwasawa, F. Sakurada, M. Iwamoto. Org. Lett. 2000, 2, 871-873.
    • (1993) Can. J. Chem. , vol.71 , pp. 611-622
    • Rogers, C.1    Keay, B.A.2
  • 50
    • 0000728738 scopus 로고    scopus 로고
    • During the intramolecular Diels-Alder reaction of furans, the equilibrium of the cycloadducts and their precursors has often been observed, see: a) C. Rogers, B. A. Keay, Can. J. Chem. 1993, 71, 611-622; b) N. Iwasawa, F. Sakurada, M. Iwamoto. Org. Lett. 2000, 2, 871-873.
    • (2000) Org. Lett. , vol.2 , pp. 871-873
    • Iwasawa, N.1    Sakurada, F.2    Iwamoto, M.3
  • 51
    • 2142782962 scopus 로고    scopus 로고
    • note
    • [10] were erroneously drawn and need to be corrected. The revised structures are shown in Scheme 4.
  • 52
    • 2142670716 scopus 로고    scopus 로고
    • note
    • 2 at 30°C for 4-6 days. In several repeated trials, optically enriched products, -4a (7-9% ee), (2R)-syn-5a (0-8% ee), and (2R)-anti-5a (0-23% ee) were obtained; however, the degree of the optical purity was small and varied. Further investigation is now being continued.
  • 53
    • 2142849977 scopus 로고    scopus 로고
    • note
    • [12a]
  • 54
    • 2042507954 scopus 로고
    • N. Miyaura, A. Suzuki. Chem. Rev. 1995, 95, 2457-2483; C.R. Johnson, B. A. Johns. J. Org. Chem. 1997, 62, 6046-6050.
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 55
    • 0030858181 scopus 로고    scopus 로고
    • N. Miyaura, A. Suzuki. Chem. Rev. 1995, 95, 2457-2483; C.R. Johnson, B. A. Johns. J. Org. Chem. 1997, 62, 6046-6050.
    • (1997) J. Org. Chem. , vol.62 , pp. 6046-6050
    • Johnson, C.R.1    Johns, B.A.2
  • 57
    • 0000176892 scopus 로고    scopus 로고
    • K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 4467-4470; H. Mosimann, P. Vogel, J. Org. Chem. 1997, 62, 3002-3007.
    • (1997) J. Org. Chem. , vol.62 , pp. 3002-3007
    • Mosimann, H.1    Vogel, P.2
  • 59
    • 0033533810 scopus 로고    scopus 로고
    • For synthetic studies, see: D. L. Wright, C. V. Robotham, K. Aboud, Tetrahedron Lett. 2002, 43, 943-946; F. E. S. Souza, R. Rodrigo, Chem. Commun. 1999, 1947-1948.
    • (1999) Chem. Commun. , pp. 1947-1948
    • Souza, F.E.S.1    Rodrigo, R.2
  • 60
    • 0033597147 scopus 로고    scopus 로고
    • For total synthesis, see: M. Takadoi, T. Katoh, A. Ishiwata, S. Terashima, Tetrahedron Lett. 1999, 40, 3399-3402; S. Chackalamannil, R. J. Davies, Y. Wang, T. Asberom, D. Doller, J. Wong, D. Leone, A. T. McPhail, J. Org. Chem. 1999, 64, 1932-1940.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3399-3402
    • Takadoi, M.1    Katoh, T.2    Ishiwata, A.3    Terashima, S.4
  • 62
    • 2142834733 scopus 로고    scopus 로고
    • note
    • Quite recently, we developed a new domino process involving a lipase-catalyzed kinetic resolution of hydroxy nitrons followed by the intramolecular [3 + 2] polar cycloaddition, which will be reported in the near future.
  • 63
    • 0034703754 scopus 로고    scopus 로고
    • For reviews, see: S. Laschat, Angew. Chem. 1996, 108, 313-315; Angew. Chem. Int. Ed. Engl. 1996, 35, 289-291; A. Ichihara, H. Oikawa, Curr. Org. Chem. 1998, 2, 365-394; G. Pohnert Chem BioChem 2001, 2, 873-875; see also: K. Auclair, A. Sutherland, J. Kennedy, D. J. Witter, J. P. Van den Heever, C. R. Hutchinson, J. C. Vederas. J. Am. Chem. Soc. 2000,. 122, 11519-11520.
    • (1996) Angew. Chem. , vol.108 , pp. 313-315
    • Laschat, S.1
  • 64
    • 33748585807 scopus 로고    scopus 로고
    • For reviews, see: S. Laschat, Angew. Chem. 1996, 108, 313-315; Angew. Chem. Int. Ed. Engl. 1996, 35, 289-291; A. Ichihara, H. Oikawa, Curr. Org. Chem. 1998, 2, 365-394; G. Pohnert Chem BioChem 2001, 2, 873-875; see also: K. Auclair, A. Sutherland, J. Kennedy, D. J. Witter, J. P. Van den Heever, C. R. Hutchinson, J. C. Vederas. J. Am. Chem. Soc. 2000,. 122, 11519-11520.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 289-291
  • 65
    • 0031837685 scopus 로고    scopus 로고
    • For reviews, see: S. Laschat, Angew. Chem. 1996, 108, 313-315; Angew. Chem. Int. Ed. Engl. 1996, 35, 289-291; A. Ichihara, H. Oikawa, Curr. Org. Chem. 1998, 2, 365-394; G. Pohnert Chem BioChem 2001, 2, 873-875; see also: K. Auclair, A. Sutherland, J. Kennedy, D. J. Witter, J. P. Van den Heever, C. R. Hutchinson, J. C. Vederas. J. Am. Chem. Soc. 2000,. 122, 11519-11520.
    • (1998) Curr. Org. Chem. , vol.2 , pp. 365-394
    • Ichihara, A.1    Oikawa, H.2
  • 66
    • 0035804164 scopus 로고    scopus 로고
    • For reviews, see: S. Laschat, Angew. Chem. 1996, 108, 313-315; Angew. Chem. Int. Ed. Engl. 1996, 35, 289-291; A. Ichihara, H. Oikawa, Curr. Org. Chem. 1998, 2, 365-394; G. Pohnert Chem BioChem 2001, 2, 873-875; see also: K. Auclair, A. Sutherland, J. Kennedy, D. J. Witter, J. P. Van den Heever, C. R. Hutchinson, J. C. Vederas. J. Am. Chem. Soc. 2000,. 122, 11519-11520.
    • (2001) ChemBioChem. , vol.2 , pp. 873-875
    • Pohnert, G.1
  • 75
    • 2142835967 scopus 로고    scopus 로고
    • note
    • 6]acetone.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.