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Volumn 59, Issue 6, 2003, Pages 857-864

Stereoselective synthesis of (-)-malyngolide, (+)-malyngolide and (+)-tanikolide using ring-closing metathesis

Author keywords

Erythrulose; Glyceraldehyde; Lactones; Malyngolide; Ring closing metathesis; Tanikolide

Indexed keywords

KETONE DERIVATIVE; LACTONE DERIVATIVE; MALYNGOLIDE; ORGANOMETALLIC COMPOUND; TANIKOLIDE; UNCLASSIFIED DRUG;

EID: 0037415524     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01594-6     Document Type: Article
Times cited : (53)

References (48)
  • 6
    • 0032572865 scopus 로고    scopus 로고
    • For two recent syntheses of (-)-1 with a comprehensive account of previous work: (a) Winter E., Hoppe D. Tetrahedron. 54:1998;10329-10338 (b) Maezaki N., Matsumori Y., Shogaki T., Soejima M., Ohishi H., Tanaka T., Iwata C. Tetrahedron. 54:1998;13087-13104. (c) For a synthesis of (+)-1: Kogure T., Eliel E.L. J. Org. Chem. 49:1984;576-579.
    • (1998) Tetrahedron , vol.54 , pp. 10329-10338
    • Winter, E.1    Hoppe, D.2
  • 7
    • 0032558597 scopus 로고    scopus 로고
    • For two recent syntheses of (-)-1 with a comprehensive account of previous work: (a) Winter E., Hoppe D. Tetrahedron. 54:1998;10329-10338 (b) Maezaki N., Matsumori Y., Shogaki T., Soejima M., Ohishi H., Tanaka T., Iwata C. Tetrahedron. 54:1998;13087-13104. (c) For a synthesis of (+)-1: Kogure T., Eliel E.L. J. Org. Chem. 49:1984;576-579.
    • (1998) Tetrahedron , vol.54 , pp. 13087-13104
    • Maezaki, N.1    Matsumori, Y.2    Shogaki, T.3    Soejima, M.4    Ohishi, H.5    Tanaka, T.6    Iwata, C.7
  • 8
    • 0021261945 scopus 로고
    • For two recent syntheses of (-)-1 with a comprehensive account of previous work: (a). (c) For a synthesis of (+)-1:
    • For two recent syntheses of (-)-1 with a comprehensive account of previous work: (a) Winter E., Hoppe D. Tetrahedron. 54:1998;10329-10338 (b) Maezaki N., Matsumori Y., Shogaki T., Soejima M., Ohishi H., Tanaka T., Iwata C. Tetrahedron. 54:1998;13087-13104. (c) For a synthesis of (+)-1: Kogure T., Eliel E.L. J. Org. Chem. 49:1984;576-579.
    • (1984) J. Org. Chem. , vol.49 , pp. 576-579
    • Kogure, T.1    Eliel, E.L.2
  • 9
    • 0342699502 scopus 로고    scopus 로고
    • For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 3631-3635
    • Kanada, R.M.1    Taniguchi, T.2    Ogasawara, K.3
  • 10
    • 0034715457 scopus 로고    scopus 로고
    • For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 10470-10471
    • Wan, Z.H.1    Nelson, S.G.2
  • 11
    • 0034649735 scopus 로고    scopus 로고
    • For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
    • (2000) Org. Lett. , pp. 4013-4015
    • Trost, B.M.1    Tang, W.P.2    Schulte, J.L.3
  • 12
    • 0034987510 scopus 로고    scopus 로고
    • For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
    • (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 645-653
    • Date, M.1    Tamai, Y.2    Hattori, T.3    Takayama, H.4    Kamikubo, Y.5    Miyano, S.6
  • 13
    • 0035979046 scopus 로고    scopus 로고
    • For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
    • (2001) Org. Lett. , pp. 1741-1744
    • Suzuki, T.1    Ohmori, K.2    Suzuki, K.3
  • 14
    • 0035801883 scopus 로고    scopus 로고
    • For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6231-6233
    • Ghosh, A.K.1    Shirai, M.2
  • 15
    • 0033913361 scopus 로고    scopus 로고
    • For syntheses of (+)-2, see: (a) Kanada R.M., Taniguchi T., Ogasawara K. Synlett. 2000;1019-1021 (b) Tanaka H., Kozuki Y., Ogasawara K. Tetrahedron Lett. 43:2002;4175-4178. For syntheses of (±)-2, see: (c) Zhang R.Z., Wang Z.Q., Wei F.P., Huang Y.R. Synth. Commun. 32:2002;2187-2194 (d) Krauss J. Nat. Prod. Lett. 15:2001;393-399. A synthesis of the unnatural enantiomer of tanikolide, (-)-2, is described in the supplementary information of Ref. 3b.
    • (2000) Synlett , pp. 1019-1021
    • Kanada, R.M.1    Taniguchi, T.2    Ogasawara, K.3
  • 16
    • 0037013913 scopus 로고    scopus 로고
    • For syntheses of (+)-2, see: (a) Kanada R.M., Taniguchi T., Ogasawara K. Synlett. 2000;1019-1021 (b) Tanaka H., Kozuki Y., Ogasawara K. Tetrahedron Lett. 43:2002;4175-4178. For syntheses of (±)-2, see: (c) Zhang R.Z., Wang Z.Q., Wei F.P., Huang Y.R. Synth. Commun. 32:2002;2187-2194 (d) Krauss J. Nat. Prod. Lett. 15:2001;393-399. A synthesis of the unnatural enantiomer of tanikolide, (-)-2, is described in the supplementary information of Ref. 3b.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4175-4178
    • Tanaka, H.1    Kozuki, Y.2    Ogasawara, K.3
  • 17
    • 0036320960 scopus 로고    scopus 로고
    • For syntheses of (+)-2, see: (a) Kanada R.M., Taniguchi T., Ogasawara K. Synlett. 2000;1019-1021 (b) Tanaka H., Kozuki Y., Ogasawara K. Tetrahedron Lett. 43:2002;4175-4178. For syntheses of (±)-2, see: (c) Zhang R.Z., Wang Z.Q., Wei F.P., Huang Y.R. Synth. Commun. 32:2002;2187-2194 (d) Krauss J. Nat. Prod. Lett. 15:2001;393-399. A synthesis of the unnatural enantiomer of tanikolide, (-)-2, is described in the supplementary information of Ref. 3b.
    • (2002) Synth. Commun. , vol.32 , pp. 2187-2194
    • Zhang, R.Z.1    Wang, Z.Q.2    Wei, F.P.3    Huang, Y.R.4
  • 18
    • 0035544148 scopus 로고    scopus 로고
    • For syntheses of (+)-2, see: (a). For syntheses of (±)-2, see: (c). A synthesis of the unnatural enantiomer of tanikolide, (-)-2, is described in the supplementary information of Ref. 3b
    • For syntheses of (+)-2, see: (a) Kanada R.M., Taniguchi T., Ogasawara K. Synlett. 2000;1019-1021 (b) Tanaka H., Kozuki Y., Ogasawara K. Tetrahedron Lett. 43:2002;4175-4178. For syntheses of (±)-2, see: (c) Zhang R.Z., Wang Z.Q., Wei F.P., Huang Y.R. Synth. Commun. 32:2002;2187-2194 (d) Krauss J. Nat. Prod. Lett. 15:2001;393-399. A synthesis of the unnatural enantiomer of tanikolide, (-)-2, is described in the supplementary information of Ref. 3b.
    • (2001) Nat. Prod. Lett. , vol.15 , pp. 393-399
    • Krauss, J.1
  • 25
    • 0012875586 scopus 로고    scopus 로고
    • note
    • The stereostructure of tosylate 5 has been further secured with the aid of an X-ray diffraction analysis. Crystallographic data (excluding structure factors) have been deposited at the Cambridge Crystallographic Data Center as supplementary material with reference CCDC-195658. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
  • 26
    • 0000220284 scopus 로고
    • (a) Lipshutz B.H., Sengupta S. Org. React. 41:1992;135-631 (b) Krause N. Modern Organocopper Chemistry. 2002;Wiley/VCH, Weinheim.
    • (1992) Org. React. , vol.41 , pp. 135-631
    • Lipshutz, B.H.1    Sengupta, S.2
  • 27
    • 0004246896 scopus 로고    scopus 로고
    • N. Krause. Weinheim: Wiley/VCH
    • (a) Lipshutz B.H., Sengupta S. Org. React. 41:1992;135-631 (b) Krause N. Modern Organocopper Chemistry. 2002;Wiley/VCH, Weinheim.
    • (2002) Modern Organocopper Chemistry
  • 28
    • 0344006321 scopus 로고    scopus 로고
    • (a) Fürstner A. Angew. Chem. Int. Ed. 39:2000;3012-3043 (b) Trnka T., Grubbs R.H. Acc. Chem. Res. 34:2001;18-29.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3012-3043
    • Fürstner, A.1
  • 29
    • 0034746687 scopus 로고    scopus 로고
    • (a) Fürstner A. Angew. Chem. Int. Ed. 39:2000;3012-3043 (b) Trnka T., Grubbs R.H. Acc. Chem. Res. 34:2001;18-29.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 18-29
    • Trnka, T.1    Grubbs, R.H.2
  • 30
    • 0012815294 scopus 로고    scopus 로고
    • note
    • This oxidation also produced small amounts (10-15%) of the oxygenation product (a cyclic ketone) at the alternative allylic position.
  • 31
    • 0036245934 scopus 로고    scopus 로고
    • Attempts at preparing lactone 10 in a more direct way by RCM of the methacrylate of alcohol 7 with the standard ruthenium catalyst were unsuccessful (see Ref. 6). Very recently, a lactone with a conjugated trisubstituted C=C bond has been prepared by means of RCM with the aid of a second-generation ruthenium catalyst: (a) Cossy J., Bauer D., Bellosta V. Synlett. 2002;715-718. However, the unsatisfactory yield in the preparation of the aforementioned methacrylate led us to disregard this alternative. See, however: (b) Rodríguez S., Castillo E., Carda M., Marco J.A. Tetrahedron. 58:2002;1185-1192.
    • (2002) Synlett , pp. 715-718
    • Cossy, J.1    Bauer, D.2    Bellosta, V.3
  • 32
    • 0037016933 scopus 로고    scopus 로고
    • Attempts at preparing lactone 10 in a more direct way by RCM of the methacrylate of alcohol 7 with the standard ruthenium catalyst were unsuccessful (see Ref. 6). Very recently, a lactone with a conjugated trisubstituted C=C bond has been prepared by means of RCM with the aid of a second-generation ruthenium catalyst: (a). However, the unsatisfactory yield in the preparation of the aforementioned methacrylate led us to disregard this alternative. See, however: (b)
    • Attempts at preparing lactone 10 in a more direct way by RCM of the methacrylate of alcohol 7 with the standard ruthenium catalyst were unsuccessful (see Ref. 6). Very recently, a lactone with a conjugated trisubstituted C=C bond has been prepared by means of RCM with the aid of a second-generation ruthenium catalyst: (a) Cossy J., Bauer D., Bellosta V. Synlett. 2002;715-718. However, the unsatisfactory yield in the preparation of the aforementioned methacrylate led us to disregard this alternative. See, however: (b) Rodríguez S., Castillo E., Carda M., Marco J.A. Tetrahedron. 58:2002;1185-1192.
    • (2002) Tetrahedron , vol.58 , pp. 1185-1192
    • Rodríguez, S.1    Castillo, E.2    Carda, M.3    Marco, J.A.4
  • 33
    • 33751386344 scopus 로고
    • (a) Wu W.-L., Wu Y.-L. J. Org. Chem. 58:1993;3586-3588 (b) Xie M., Berges D.A., Robins M.J. J. Org. Chem. 61:1996;5178-5179.
    • (1993) J. Org. Chem. , vol.58 , pp. 3586-3588
    • Wu, W.-L.1    Wu, Y.-L.2
  • 35
    • 0012768220 scopus 로고    scopus 로고
    • note
    • 4 were unsuccessful, however, and led only to reduction of the lactone carbonyl group.
  • 37
    • 0012875587 scopus 로고    scopus 로고
    • note
    • The reduction of the aldehyde function in the intermediate products resulting from oxidative cleavage of 10, ent-10 and 17 has to be performed at low temperature, otherwise reductive opening of the lactone ring becomes competitive.
  • 38
    • 0012769518 scopus 로고    scopus 로고
    • Part of the data presented here have been taken from the PhD Thesis of E. Castillo (Univ. Jaume I, Castellón, Spain, 2000)
    • Part of the data presented here have been taken from the PhD Thesis of E. Castillo (Univ. Jaume I, Castellón, Spain, 2000).
  • 39
    • 0012815295 scopus 로고    scopus 로고
    • Products of Michael addition to the conjugated double bond were detected during attempts at hydrolytic cleavage of the acetonide moiety in 15. In view of this, acetal hydrolysis was performed in saturated lactone 16 under carefully controlled conditions, as this compound was prone to translactonization and/or hydrolytic ring opening in acidic media
    • Products of Michael addition to the conjugated double bond were detected during attempts at hydrolytic cleavage of the acetonide moiety in 15. In view of this, acetal hydrolysis was performed in saturated lactone 16 under carefully controlled conditions, as this compound was prone to translactonization and/or hydrolytic ring opening in acidic media.
  • 40
    • 0012827099 scopus 로고    scopus 로고
    • Stronger Lewis acids caused destruction of the acetonide moiety (see Refs. 7 and 9)
    • Stronger Lewis acids caused destruction of the acetonide moiety (see Refs. 7 and 9).
  • 42
    • 0036329749 scopus 로고    scopus 로고
    • For recent contributions of our group, see: (a) Carda M., González F., Castillo E., Rodríguez S., Marco J.A., Eur. J. Org. Chem. 2002;2649-2655 (b) Carda M., Rodríguez S., Segovia B., Marco J.A. J. Org. Chem. 67:2002;6560-6563 (c) Murga J., Falomir E., García-Fortanet J., Carda M., Marco J.A. Org. Lett. 2002;3447-3449 (d) Falomir E., Murga J., Carda M., Marco J.A. Tetrahedron Lett. 44:2003;539-541.
    • (2002) J. Org. Chem. , pp. 2649-2655
    • Carda, M.1    González, F.2    Castillo, E.3    Rodríguez, S.4    Marco, J.A.5    Eur6
  • 43
    • 0037031711 scopus 로고    scopus 로고
    • For recent contributions of our group, see: (a) Carda M., González F., Castillo E., Rodríguez S., Marco J.A., Eur. J. Org. Chem. 2002;2649-2655 (b) Carda M., Rodríguez S., Segovia B., Marco J.A. J. Org. Chem. 67:2002;6560-6563 (c) Murga J., Falomir E., García-Fortanet J., Carda M., Marco J.A. Org. Lett. 2002;3447-3449 (d) Falomir E., Murga J., Carda M., Marco J.A. Tetrahedron Lett. 44:2003;539-541.
    • (2002) J. Org. Chem. , vol.67 , pp. 6560-6563
    • Carda, M.1    Rodríguez, S.2    Segovia, B.3    Marco, J.A.4
  • 44
    • 0037015429 scopus 로고    scopus 로고
    • For recent contributions of our group, see: (a) Carda M., González F., Castillo E., Rodríguez S., Marco J.A., Eur. J. Org. Chem. 2002;2649-2655 (b) Carda M., Rodríguez S., Segovia B., Marco J.A. J. Org. Chem. 67:2002;6560-6563 (c) Murga J., Falomir E., García-Fortanet J., Carda M., Marco J.A. Org. Lett. 2002;3447-3449 (d) Falomir E., Murga J., Carda M., Marco J.A. Tetrahedron Lett. 44:2003;539-541.
    • (2002) Org. Lett. , pp. 3447-3449
    • Murga, J.1    Falomir, E.2    García-Fortanet, J.3    Carda, M.4    Marco, J.A.5
  • 45
    • 0037433978 scopus 로고    scopus 로고
    • For recent contributions of our group, see: (a)
    • For recent contributions of our group, see: (a) Carda M., González F., Castillo E., Rodríguez S., Marco J.A., Eur. J. Org. Chem. 2002;2649-2655 (b) Carda M., Rodríguez S., Segovia B., Marco J.A. J. Org. Chem. 67:2002;6560-6563 (c) Murga J., Falomir E., García-Fortanet J., Carda M., Marco J.A. Org. Lett. 2002;3447-3449 (d) Falomir E., Murga J., Carda M., Marco J.A. Tetrahedron Lett. 44:2003;539-541.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 539-541
    • Falomir, E.1    Murga, J.2    Carda, M.3    Marco, J.A.4


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