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Volumn 13, Issue 18, 2007, Pages 5135-5150

Dienyne ring-closing metathesis approach for the construction of taxosteroids

Author keywords

Medium ring compounds; Metathesis; Ring closing dienyne metathesis (RCDEYM); Steroid analogues; Taxosteroids

Indexed keywords

CARBON; CYCLIZATION; HYBRID MATERIALS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

EID: 34250854630     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601685     Document Type: Article
Times cited : (26)

References (106)
  • 1
    • 0036430152 scopus 로고    scopus 로고
    • For review, see: a
    • For review, see: a) G. Mehta, V. Singh, Chem. Soc. Rev. 2002, 31, 324-334;
    • (2002) Chem. Soc. Rev , vol.31 , pp. 324-334
    • Mehta, G.1    Singh, V.2
  • 3
    • 0141427680 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 3996-4028, .
    • (2003) Chem. Int. Ed , vol.42 , pp. 3996-4028
    • Angew1
  • 5
    • 0028878549 scopus 로고    scopus 로고
    • For a study of the construction of the bicyclo[5.3.1]undecene system on the steroid BCD system by Diels-Alder reaction, see: T. K. Park, I. J. Kim, S. J. Danishefsky, S. de Gala, Tetrahedron Lett. 1995, 36, 1019-1022.
    • For a study of the construction of the bicyclo[5.3.1]undecene system on the steroid BCD system by Diels-Alder reaction, see: T. K. Park, I. J. Kim, S. J. Danishefsky, S. de Gala, Tetrahedron Lett. 1995, 36, 1019-1022.
  • 6
    • 0003469887 scopus 로고
    • Ed, M. Suffness, CRC, Boca Raton
    • a) Taxol: Science and Applications (Ed.: M. Suffness), CRC, Boca Raton, 1995;
    • (1995) Taxol: Science and Applications
  • 17
    • 0002174828 scopus 로고
    • For reviews, see: a, Ed, Atta-ur-Rahman, Elsevier, Amsterdam
    • For reviews, see: a) T. Oishi, Y. Ohtsuka in Studies in Natural Products Synthesis, Vol.3 (Ed.: Atta-ur-Rahman), Elsevier, Amsterdam, 1989, pp. 73-115;
    • (1989) Studies in Natural Products Synthesis , vol.3 , pp. 73-115
    • Oishi, T.1    Ohtsuka, Y.2
  • 22
    • 0001410979 scopus 로고
    • For reviews see: a
    • For reviews see: a) H. M. R. Hoffmann, Angew. Chem. 1992, 104, 1361-1363;
    • (1992) Angew. Chem , vol.104 , pp. 1361-1363
    • Hoffmann, H.M.R.1
  • 28
  • 30
    • 0035907919 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 2224-2248.
    • (2001) Chem. Int. Ed , vol.40 , pp. 2224-2248
    • Angew1
  • 31
    • 1442360753 scopus 로고    scopus 로고
    • For reviews on metathesis, see: a, Ed, R. H. Grubbs, Wiley-VCH, Weinheim
    • For reviews on metathesis, see: a) Handbook of Metathesis (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, 2003;
    • (2003) Handbook of Metathesis
  • 33
    • 0344006321 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 3012-3043, ;
    • (2000) Chem. Int. Ed , vol.39 , pp. 3012-3043
    • Angew1
  • 36
    • 0038215596 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1900-1923.
    • (2003) Chem. Int. Ed , vol.42 , pp. 1900-1923
    • Angew1
  • 37
    • 0000402646 scopus 로고    scopus 로고
    • For a view on the synthesis of medium-sized rings by RCM, see: e
    • For a view on the synthesis of medium-sized rings by RCM, see: e) M. E. Maier, Angew. Chem. 2000, 112, 2153-2157;
    • (2000) Angew. Chem , vol.112 , pp. 2153-2157
    • Maier, M.E.1
  • 38
    • 0034674322 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 2073-2077.
    • (2000) Chem. Int. Ed , vol.39 , pp. 2073-2077
    • Angew1
  • 39
    • 22744453115 scopus 로고    scopus 로고
    • For a review on metathesis reactions in total synthesis, see: f
    • For a review on metathesis reactions in total synthesis, see: f) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564-4601;
    • (2005) Angew. Chem , vol.117 , pp. 4564-4601
    • Nicolaou, K.C.1    Bulger, P.G.2    Sarlah, D.3
  • 40
    • 22744448499 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4490-4527.
    • (2005) Chem. Int. Ed , vol.44 , pp. 4490-4527
    • Angew1
  • 41
    • 0000747644 scopus 로고    scopus 로고
    • For some examples of dienyne metathesis, see: a
    • For some examples of dienyne metathesis, see: a) J. Renaud, C.-D. Graf, L. Oberer, Angew. Chem. 2000, 112, 3231-3234;
    • (2000) Angew. Chem , vol.112 , pp. 3231-3234
    • Renaud, J.1    Graf, C.-D.2    Oberer, L.3
  • 42
    • 0034283391 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 3101-3104;
    • (2000) Chem. Int. Ed , vol.39 , pp. 3101-3104
    • Angew1
  • 52
    • 1842483218 scopus 로고    scopus 로고
    • For reviews on enyne metathesis, see: a
    • For reviews on enyne metathesis, see: a) S.T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317-1382;
    • (2004) Chem. Rev , vol.104 , pp. 1317-1382
    • Diver, S.T.1    Giessert, A.J.2
  • 54
    • 3042782211 scopus 로고    scopus 로고
    • Ed, R. H. Grubbs, Wiley-VCH, Weinheim
    • c) M. Mori in Handbook of Metathesis, Vol. 2 (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, 2003, pp. 176-204;
    • (2003) Handbook of Metathesis , vol.2 , pp. 176-204
    • Mori, M.1
  • 59
    • 0037118326 scopus 로고    scopus 로고
    • Our original studies on analogues of the putative transition state of the isomerization of previtamin D, to vitamin D3 showed that formation of the eight-membered B ring by RCM is possible only if the constraints introduced by the A ring are not present. a E. M. Codesido, J. R. Rodríguez, L. Castedo, J. R. Granja, Org. Lett. 2002, 4, 1651-1654;
    • 3 showed that formation of the eight-membered B ring by RCM is possible only if the constraints introduced by the A ring are not present. a) E. M. Codesido, J. R. Rodríguez, L. Castedo, J. R. Granja, Org. Lett. 2002, 4, 1651-1654;
  • 67
    • 34250889913 scopus 로고    scopus 로고
    • For convenience, steroid numbering is used (see Figure 1).
    • For convenience, steroid numbering is used (see Figure 1).
  • 68
    • 0037036803 scopus 로고    scopus 로고
    • For different reactivities of RCM substrates depending on the relative configuration, see: a
    • For different reactivities of RCM substrates depending on the relative configuration, see: a) M. Ogasawara, T. Nagano, T. Hayasi, J. Am. Chem. Soc. 2002, 124, 9068-9069;
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 9068-9069
    • Ogasawara, M.1    Nagano, T.2    Hayasi, T.3
  • 73
    • 19744379693 scopus 로고    scopus 로고
    • For a recent enyne ring-closing metathesis mechanism studies, see: a
    • For a recent enyne ring-closing metathesis mechanism studies, see: a) J. J. Lippstreu, B. F. Straub, J. Am. Chem. Soc. 2005, 127, 7444-7457.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 7444-7457
    • Lippstreu, J.J.1    Straub, B.F.2
  • 74
    • 0034734307 scopus 로고    scopus 로고
    • For RCM mechanism studies, see: b
    • For RCM mechanism studies, see: b) C. Adlhart, P. Hofmann, P. Chen, J. Am. Chem. Soc. 2000, 122, 8204-8214;
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 8204-8214
    • Adlhart, C.1    Hofmann, P.2    Chen, P.3
  • 80
    • 0026101278 scopus 로고    scopus 로고
    • 3. see: J. L. Mascareñas, L. Sarandeses, L. Castedo, A. Mouriño, Tetrahedron 1991, 47, 3485-3498.
    • 3. see: J. L. Mascareñas, L. Sarandeses, L. Castedo, A. Mouriño, Tetrahedron 1991, 47, 3485-3498.
  • 81
    • 34250902818 scopus 로고    scopus 로고
    • 10R.
    • 10R.
  • 82
    • 34250814108 scopus 로고    scopus 로고
    • After purification on silica gel (see Ref. [21]).
    • After purification on silica gel (see Ref. [21]).
  • 87
    • 34250883715 scopus 로고    scopus 로고
    • 10S derivative to RCM conditions with 10a as catalyst afforded 13b in 87% yield together with a small amount of triene 16b; no 11a was observed (Table 1, Entry 4).
    • 10S derivative to RCM conditions with 10a as catalyst afforded 13b in 87% yield together with a small amount of triene 16b; no 11a was observed (Table 1, Entry 4).
  • 88
    • 27444446247 scopus 로고    scopus 로고
    • Ed, R. Mahrwald, Wiley-VCH, Weinheim
    • a) Modern Aldol Reactions, Vols. 1, 2 (Ed.: R. Mahrwald), Wiley-VCH, Weinheim, 2004;
    • (2004) Modern Aldol Reactions, Vols. 1, 2
  • 92
    • 33845219123 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7506-7525.
    • (2006) Chem. Int. Ed , vol.45 , pp. 7506-7525
    • Angew1
  • 93
    • 34250796037 scopus 로고    scopus 로고
    • Note that the 10 S series in 9h-j corresponds to the 10R series in 9a-g due to the presence of the C19 hydroxy group.
    • Note that the 10 S series in 9h-j corresponds to the 10R series in 9a-g due to the presence of the C19 hydroxy group.
  • 94
    • 0033824780 scopus 로고    scopus 로고
    • It has been proposed that the presence of two nucleophilic hydroxy groups promotes decomposition of the catalyst, see: a L. Hyldtoft, R. Madsen, J. Am. Chem. Soc. 2000, 122, 8444-8452;
    • It has been proposed that the presence of two nucleophilic hydroxy groups promotes decomposition of the catalyst, see: a) L. Hyldtoft, R. Madsen, J. Am. Chem. Soc. 2000, 122, 8444-8452;
  • 96
    • 34250824493 scopus 로고    scopus 로고
    • 10S.
    • 10S.
  • 97
    • 9344256087 scopus 로고    scopus 로고
    • For some studies of regioselectivity on RCEYM reaction, see: a
    • For some studies of regioselectivity on RCEYM reaction, see: a) E. C. Hansen, D. Lee, J. Am. Chem. Soc. 2004, 126, 15 074-15 080;
    • (2004) J. Am. Chem. Soc , vol.126
    • Hansen, E.C.1    Lee, D.2
  • 99
    • 0035915149 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 4274-4277.
    • (2001) Chem. Int. Ed , vol.40 , pp. 4274-4277
    • Angew1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.