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Volumn 1996, Issue 2, 1996, Pages 175-176

A New Facile Pinane Approach to Taxoid Systems Based on trans-Verbenol

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Indexed keywords


EID: 1842539486     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5348     Document Type: Article
Times cited : (2)

References (26)
  • 4
    • 0028012837 scopus 로고
    • The first two total syntheses of taxol have recently appeared: a) Holton, R. A.; Somoza, C.; Kim. H.; Liang, F.; Biediger, R.; Boatman, P.; Shindo, M.; Smith, C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K.; Gentile, L.; Liu, J. J. Am. Chem. Soc. 1994, 116, 1597, 1599. b) Nicolaou, K. C.; Yang, Z.; Liu, J.; Ueno, H.; Nantermet, P.; Guy, R.; Claiborne, C.; Renaud, J.; Couladouros, E.; Paulvannan, K.; Sorensen, E. Nature 1994, 367, 630.
    • (1994) Nature , vol.367 , pp. 630
    • Nicolaou, K.C.1    Yang, Z.2    Liu, J.3    Ueno, H.4    Nantermet, P.5    Guy, R.6    Claiborne, C.7    Renaud, J.8    Couladouros, E.9    Paulvannan, K.10    Sorensen, E.11
  • 5
    • 84943510383 scopus 로고
    • For excellent recent reviews on the synthesis of taxanes, see a) Swindell, C. S. Org. Prep. Procedures. Int. 1992, 23, 465; b) Nicolaou, K. C.; Dai, W.; Guy, R. Angew. Chem. Int. Ed. Engl. 1994, 33, 15. c) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemporary Organic Synthesis, 1994, 47.
    • (1992) Org. Prep. Procedures. Int. , vol.23 , pp. 465
    • Swindell, C.S.1
  • 6
    • 33748226949 scopus 로고
    • For excellent recent reviews on the synthesis of taxanes, see a) Swindell, C. S. Org. Prep. Procedures. Int. 1992, 23, 465; b) Nicolaou, K. C.; Dai, W.; Guy, R. Angew. Chem. Int. Ed. Engl. 1994, 33, 15. c) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemporary Organic Synthesis, 1994, 47.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 15
    • Nicolaou, K.C.1    Dai, W.2    Guy, R.3
  • 7
    • 0002502917 scopus 로고
    • For excellent recent reviews on the synthesis of taxanes, see a) Swindell, C. S. Org. Prep. Procedures. Int. 1992, 23, 465; b) Nicolaou, K. C.; Dai, W.; Guy, R. Angew. Chem. Int. Ed. Engl. 1994, 33, 15. c) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemporary Organic Synthesis, 1994, 47.
    • (1994) Contemporary Organic Synthesis , pp. 47
    • Boa, A.N.1    Jenkins, P.R.2    Lawrence, N.J.3
  • 14
    • 0001635506 scopus 로고
    • The photochemical version of pinene approach based upon photoisomerisation of Verbenone to Chrysanthenone was independently disclosed a) Wender, P. A.; Mucciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878. b) Winkler, J. D.; Bhattacharya, S. K.; Liotta, F.; Batey, R. A.; Heffermann, G. D.; Cladingboel, D. E.; Kelly, R. C. Tetrahedron Lett. 1995, 36, 2211 and referrences cited therein.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5878
    • Wender, P.A.1    Mucciaro, T.P.2
  • 15
    • 0028931514 scopus 로고
    • and referrences cited therein
    • The photochemical version of pinene approach based upon photoisomerisation of Verbenone to Chrysanthenone was independently disclosed a) Wender, P. A.; Mucciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878. b) Winkler, J. D.; Bhattacharya, S. K.; Liotta, F.; Batey, R. A.; Heffermann, G. D.; Cladingboel, D. E.; Kelly, R. C. Tetrahedron Lett. 1995, 36, 2211 and referrences cited therein.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2211
    • Winkler, J.D.1    Bhattacharya, S.K.2    Liotta, F.3    Batey, R.A.4    Heffermann, G.D.5    Cladingboel, D.E.6    Kelly, R.C.7
  • 16
    • 85033747454 scopus 로고    scopus 로고
    • note
    • 25= - 42°(neat)}a component of Indian turpentine oil.
  • 17
    • 84970605889 scopus 로고
    • 12 in pyrolysis and isolation techniques helped us to make this improvement over the reported yield of 21%, see Escher S., Giersch. W., Ohloff. G. Helv.Chim.Acta. 1981, 64 ,943.
    • (1981) Helv.Chim.Acta , vol.64 , pp. 943
    • Escher, S.1    Giersch, W.2    Ohloff, G.3
  • 18
    • 85033753901 scopus 로고    scopus 로고
    • note
    • A 1% solution of trans-Verbenol in n-hexane was pyrolysed by downward passage through a quartz tube (100 cm.x 1.3 cm) at 350°C in a current of N at the rate of 12 ml/min. Separation and purification was carried out by column chromatography on Silica gel instead of making the adduct as reported. These operations have resulted in improvement in the yield of 8from 21% to 38%.
  • 20
    • 85033757363 scopus 로고    scopus 로고
    • note
    • 16O: C, 80.48; H, 9.76: Found: C, 80.36; H, 9.82.
  • 21
    • 85033749827 scopus 로고    scopus 로고
    • note
    • As mentioned above, it may be noted that these intermediates 11 and 12 have been synthesised using much costlier (+)-Hajos-Parrish ketone over a number of steps.
  • 24
    • 85033754175 scopus 로고    scopus 로고
    • note
    • 2: C,79.06; H,8.53. Found; C,79.28; H,8.42.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.