메뉴 건너뛰기




Volumn 27, Issue 1, 2003, Pages 50-59

Chemoenzymatic total syntheses of the sesquiterpene (-)-patchoulenone

Author keywords

[No Author keywords available]

Indexed keywords

2,3,7,8 TETRAHYDRO 4,5,5 TRIMETHYL 8 (PHENYLMETHOXY) 1H 3A 7 METHANOAZULEN 8A(6H) OL; ALCOHOL; ANION; BICYCLO[2.2.2]OCTENONE; BICYCLO[5.3.1]UNDEC 7(8) ENONE; CARBON; CHEMICAL COMPOUND; CHLORIDE; DIENESTROL; ETHER DERIVATIVE; HEXAHYDRO 4,9,9 TRIMETHYL 1H 3A 7 METHANOAZULENE 8 8A(4H) DIOL; HEXAHYDRO 4,9,9 TRIMETHYL 8 (PHENYLMETHOXY) 1H 3A 7 METHANOAZULENE 4 8A OXIDE; HYDROGEN; ISOPROPENYLLITHIUM; KETONE; KETONE DERIVATIVE; LITHIUM DERIVATIVE; METHYL GROUP; OXIDE; PALLADIUM; PATCHOULENONE; REAGENT; SESQUITERPENE; TERPENE DERIVATIVE; THIOPHENOL; TIN; UNCLASSIFIED DRUG;

EID: 0037243543     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b206372g     Document Type: Article
Times cited : (34)

References (50)
  • 10
    • 0002748323 scopus 로고
    • For reviews on the applications of cis-1,2-dihydrocatechols in synthesis see: (a) D. A. Widdowson, D. W. Ribbons and S. D. Thomas, Janssen Chim. Acta, 1990, 8, 3; (b) H. A. J. Carless, Tetrahedron: Asymmetry, 1992, 3, 795; (c) S. M. Brown and T. Hudlicky, in Organic Synthesis: Theory and Applications, ed. T. Hudlicky, JAI, Greenwich, CT, 1993, vol. 2, p. 113; (d) T. Hudlicky and J. W. Reed, in Advances in Asymmetric Synthesis, ed. A. Hassner, JAI, Greenwich, CT, 1995, vol. 1, p. 271; (e) T. Hudlicky and A. J. Thorpe, Chem. Commun., 1996, 1993; (f) T. Hudlicky, D. Gonzalez and D. T. Gibson, Aldrichimica Acta, 1999, 32, 35.
    • (1990) Janssen Chim. Acta , vol.8 , pp. 3
    • Widdowson, D.A.1    Ribbons, D.W.2    Thomas, S.D.3
  • 11
    • 0026659843 scopus 로고
    • For reviews on the applications of cis-1,2-dihydrocatechols in synthesis see: (a) D. A. Widdowson, D. W. Ribbons and S. D. Thomas, Janssen Chim. Acta, 1990, 8, 3; (b) H. A. J. Carless, Tetrahedron: Asymmetry, 1992, 3, 795; (c) S. M. Brown and T. Hudlicky, in Organic Synthesis: Theory and Applications, ed. T. Hudlicky, JAI, Greenwich, CT, 1993, vol. 2, p. 113; (d) T. Hudlicky and J. W. Reed, in Advances in Asymmetric Synthesis, ed. A. Hassner, JAI, Greenwich, CT, 1995, vol. 1, p. 271; (e) T. Hudlicky and A. J. Thorpe, Chem. Commun., 1996, 1993; (f) T. Hudlicky, D. Gonzalez and D. T. Gibson, Aldrichimica Acta, 1999, 32, 35.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 795
    • Carless, H.A.J.1
  • 12
    • 0001345541 scopus 로고
    • ed. T. Hudlicky, JAI, Greenwich, CT
    • For reviews on the applications of cis-1,2-dihydrocatechols in synthesis see: (a) D. A. Widdowson, D. W. Ribbons and S. D. Thomas, Janssen Chim. Acta, 1990, 8, 3; (b) H. A. J. Carless, Tetrahedron: Asymmetry, 1992, 3, 795; (c) S. M. Brown and T. Hudlicky, in Organic Synthesis: Theory and Applications, ed. T. Hudlicky, JAI, Greenwich, CT, 1993, vol. 2, p. 113; (d) T. Hudlicky and J. W. Reed, in Advances in Asymmetric Synthesis, ed. A. Hassner, JAI, Greenwich, CT, 1995, vol. 1, p. 271; (e) T. Hudlicky and A. J. Thorpe, Chem. Commun., 1996, 1993; (f) T. Hudlicky, D. Gonzalez and D. T. Gibson, Aldrichimica Acta, 1999, 32, 35.
    • (1993) Organic Synthesis: Theory and Applications , vol.2 , pp. 113
    • Brown, S.M.1    Hudlicky, T.2
  • 13
    • 0002485317 scopus 로고
    • ed. A. Hassner, JAI, Greenwich, CT
    • For reviews on the applications of cis-1,2-dihydrocatechols in synthesis see: (a) D. A. Widdowson, D. W. Ribbons and S. D. Thomas, Janssen Chim. Acta, 1990, 8, 3; (b) H. A. J. Carless, Tetrahedron: Asymmetry, 1992, 3, 795; (c) S. M. Brown and T. Hudlicky, in Organic Synthesis: Theory and Applications, ed. T. Hudlicky, JAI, Greenwich, CT, 1993, vol. 2, p. 113; (d) T. Hudlicky and J. W. Reed, in Advances in Asymmetric Synthesis, ed. A. Hassner, JAI, Greenwich, CT, 1995, vol. 1, p. 271; (e) T. Hudlicky and A. J. Thorpe, Chem. Commun., 1996, 1993; (f) T. Hudlicky, D. Gonzalez and D. T. Gibson, Aldrichimica Acta, 1999, 32, 35.
    • (1995) Advances in Asymmetric Synthesis , vol.1 , pp. 271
    • Hudlicky, T.1    Reed, J.W.2
  • 14
    • 0001854468 scopus 로고    scopus 로고
    • For reviews on the applications of cis-1,2-dihydrocatechols in synthesis see: (a) D. A. Widdowson, D. W. Ribbons and S. D. Thomas, Janssen Chim. Acta, 1990, 8, 3; (b) H. A. J. Carless, Tetrahedron: Asymmetry, 1992, 3, 795; (c) S. M. Brown and T. Hudlicky, in Organic Synthesis: Theory and Applications, ed. T. Hudlicky, JAI, Greenwich, CT, 1993, vol. 2, p. 113; (d) T. Hudlicky and J. W. Reed, in Advances in Asymmetric Synthesis, ed. A. Hassner, JAI, Greenwich, CT, 1995, vol. 1, p. 271; (e) T. Hudlicky and A. J. Thorpe, Chem. Commun., 1996, 1993; (f) T. Hudlicky, D. Gonzalez and D. T. Gibson, Aldrichimica Acta, 1999, 32, 35.
    • (1996) Chem. Commun. , pp. 1993
    • Hudlicky, T.1    Thorpe, A.J.2
  • 15
    • 0001846314 scopus 로고    scopus 로고
    • For reviews on the applications of cis-1,2-dihydrocatechols in synthesis see: (a) D. A. Widdowson, D. W. Ribbons and S. D. Thomas, Janssen Chim. Acta, 1990, 8, 3; (b) H. A. J. Carless, Tetrahedron: Asymmetry, 1992, 3, 795; (c) S. M. Brown and T. Hudlicky, in Organic Synthesis: Theory and Applications, ed. T. Hudlicky, JAI, Greenwich, CT, 1993, vol. 2, p. 113; (d) T. Hudlicky and J. W. Reed, in Advances in Asymmetric Synthesis, ed. A. Hassner, JAI, Greenwich, CT, 1995, vol. 1, p. 271; (e) T. Hudlicky and A. J. Thorpe, Chem. Commun., 1996, 1993; (f) T. Hudlicky, D. Gonzalez and D. T. Gibson, Aldrichimica Acta, 1999, 32, 35.
    • (1999) Aldrichimica Acta , vol.32 , pp. 35
    • Hudlicky, T.1    Gonzalez, D.2    Gibson, D.T.3
  • 18
    • 0001290261 scopus 로고
    • eds. B. Trost and I. Fleming, Pergamon Press, Oxford
    • For reviews on the Prins and related carbonyl-ene reactions see: (a) B. B. Snider, in Comprehensive Organic Synthesis, eds. B. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 2, p. 527; (b) D. R. Adams and S. P. Bhatnagar, Synthesis, 1977, 661. For some recent articles concerning the mechanism of the carbonyl-ene cyclisation reaction see: (c) J. A. Marshall and M. W. Andersen, J. Org. Chem., 1992, 57, 5851; (d) D. C. Braddock, K. K. Hii and J. M. Brown, Angew Chem., Int. Ed., 1998, 37, 1720.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 527
    • Snider, B.B.1
  • 19
    • 85038030159 scopus 로고
    • For reviews on the Prins and related carbonyl-ene reactions see: (a) B. B. Snider, in Comprehensive Organic Synthesis, eds. B. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 2, p. 527; (b) D. R. Adams and S. P. Bhatnagar, Synthesis, 1977, 661. For some recent articles concerning the mechanism of the carbonyl-ene cyclisation reaction see: (c) J. A. Marshall and M. W. Andersen, J. Org. Chem., 1992, 57, 5851; (d) D. C. Braddock, K. K. Hii and J. M. Brown, Angew Chem., Int. Ed., 1998, 37, 1720.
    • (1977) Synthesis , pp. 661
    • Adams, D.R.1    Bhatnagar, S.P.2
  • 20
    • 0000087777 scopus 로고
    • For reviews on the Prins and related carbonyl-ene reactions see: (a) B. B. Snider, in Comprehensive Organic Synthesis, eds. B. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 2, p. 527; (b) D. R. Adams and S. P. Bhatnagar, Synthesis, 1977, 661. For some recent articles concerning the mechanism of the carbonyl-ene cyclisation reaction see: (c) J. A. Marshall and M. W. Andersen, J. Org. Chem., 1992, 57, 5851; (d) D. C. Braddock, K. K. Hii and J. M. Brown, Angew Chem., Int. Ed., 1998, 37, 1720.
    • (1992) J. Org. Chem. , vol.57 , pp. 5851
    • Marshall, J.A.1    Andersen, M.W.2
  • 21
    • 0344936041 scopus 로고    scopus 로고
    • For reviews on the Prins and related carbonyl-ene reactions see: (a) B. B. Snider, in Comprehensive Organic Synthesis, eds. B. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 2, p. 527; (b) D. R. Adams and S. P. Bhatnagar, Synthesis, 1977, 661. For some recent articles concerning the mechanism of the carbonyl-ene cyclisation reaction see: (c) J. A. Marshall and M. W. Andersen, J. Org. Chem., 1992, 57, 5851; (d) D. C. Braddock, K. K. Hii and J. M. Brown, Angew Chem., Int. Ed., 1998, 37, 1720.
    • (1998) Angew Chem., Int. Ed. , vol.37 , pp. 1720
    • Braddock, D.C.1    Hii, K.K.2    Brown, J.M.3
  • 22
    • 0012645801 scopus 로고
    • Oxetane formation has been observed during the course of an intermolecular carbonyl-ene reaction: H. Kwart and M. Brechbiel, J. Org. Chem., 1982, 47, 5409. We are not aware of any examples of oxetane formation being observed during the course of a Prins reaction.
    • (1982) J. Org. Chem. , vol.47 , pp. 5409
    • Kwart, H.1    Brechbiel, M.2
  • 23
    • 37049121248 scopus 로고
    • For related examples of intramolecular Paterno-Büchi reactions see: (a) J. Meinwald and A. T. Hamner, J. Chem Soc., Chem. Commun., 1969, 1302; (b) G. L. Lange and M. Bosch, Tetrahedron Lett., 1971, 315; (c) C. A. Dvorak, C. Dufour, S. Iwasa and V. H. Rawal, J. Org. Chem., 1998, 63, 5302.
    • (1969) J. Chem Soc., Chem. Commun. , pp. 1302
    • Meinwald, J.1    Hamner, A.T.2
  • 24
    • 0012646797 scopus 로고
    • For related examples of intramolecular Paterno-Büchi reactions see: (a) J. Meinwald and A. T. Hamner, J. Chem Soc., Chem. Commun., 1969, 1302; (b) G. L. Lange and M. Bosch, Tetrahedron Lett., 1971, 315; (c) C. A. Dvorak, C. Dufour, S. Iwasa and V. H. Rawal, J. Org. Chem., 1998, 63, 5302.
    • (1971) Tetrahedron Lett. , pp. 315
    • Lange, G.L.1    Bosch, M.2
  • 25
    • 0012647320 scopus 로고    scopus 로고
    • For related examples of intramolecular Paterno-Büchi reactions see: (a) J. Meinwald and A. T. Hamner, J. Chem Soc., Chem. Commun., 1969, 1302; (b) G. L. Lange and M. Bosch, Tetrahedron Lett., 1971, 315; (c) C. A. Dvorak, C. Dufour, S. Iwasa and V. H. Rawal, J. Org. Chem., 1998, 63, 5302.
    • (1998) J. Org. Chem. , vol.63 , pp. 5302
    • Dvorak, C.A.1    Dufour, C.2    Iwasa, S.3    Rawal, V.H.4
  • 26
    • 4244147127 scopus 로고
    • Br. Pat. 1 205 397 (Cl.c 07c), 1970
    • 2 see: G. Foster and P. Johnson, Br. Pat. 1 205 397 (Cl.c 07c), 1970 (Chem. Abs., 1970, 73, 131809a).
    • (1970) Chem. Abs. , vol.73
    • Foster, G.1    Johnson, P.2
  • 27
    • 0001764957 scopus 로고
    • G. A. Molander and C. Kenny, J. Am. Chem. Soc., 1989, 111, 8236. For a useful recent review of this type of reduction/cyclisation sequence see: G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8236
    • Molander, G.A.1    Kenny, C.2
  • 28
    • 2142715741 scopus 로고    scopus 로고
    • G. A. Molander and C. Kenny, J. Am. Chem. Soc., 1989, 111, 8236. For a useful recent review of this type of reduction/cyclisation sequence see: G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307.
    • (1996) Chem. Rev. , vol.96 , pp. 307
    • Molander, G.A.1    Harris, C.R.2
  • 30
    • 1242352716 scopus 로고
    • -1. (a) D. P. Curran, T. L. Fevig, C. P. Jasperse and M. J. Totleben, Synlett, 1992, 943; (b) M. J. Gibian and R. C. Corley, Chem. Rev., 1973, 73, 441.
    • (1973) Chem. Rev. , vol.73 , pp. 441
    • Gibian, M.J.1    Corley, R.C.2
  • 31
    • 0012649764 scopus 로고    scopus 로고
    • note
    • 2 and di-iodomethane) in THF-HMPA does not lead to any reaction.
  • 32
    • 0012652439 scopus 로고
    • 20b promoted reductive cyclisation of compound 6 should afford target 12 but these processes proved to be very inefficient. (a) K. J. Kulicke, Synlett, 1992, 91; (b) E. J. Enholm, Tetrahedron Lett., 1989, 37, 4939.
    • (1992) Synlett , pp. 91
    • Kulicke, K.J.1
  • 33
    • 0000860816 scopus 로고
    • 20b promoted reductive cyclisation of compound 6 should afford target 12 but these processes proved to be very inefficient. (a) K. J. Kulicke, Synlett, 1992, 91; (b) E. J. Enholm, Tetrahedron Lett., 1989, 37, 4939.
    • (1989) Tetrahedron Lett. , vol.37 , pp. 4939
    • Enholm, E.J.1
  • 37
    • 0012646444 scopus 로고    scopus 로고
    • note
    • Ketone 13 was prepared by the route detailed in the Experimental.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.