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1
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0015211527
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Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T.; J. Am. Chem. Soc. 1971, 93, 2325.
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Wani, M.C.1
Taylor, H.L.2
Wall, M.E.3
Coggon, P.4
McPhail, A.T.5
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3
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0028213668
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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.
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Holton, R.A.1
Somoza, C.2
Kim, H.3
Liang, F.4
Biediger, R.5
Boatman, P.6
Shindo, M.7
Smith, C.8
Kim, S.9
Nadizadeh, H.10
Suzuki, Y.11
Tao, C.12
Vu, P.13
Tang, S.14
Zhang, P.15
Murthi, K.16
Gentile, L.17
Liu, J.18
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4
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0028012837
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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.
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Nature
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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
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5
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84943510383
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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.
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Org. Prep. Procedures. Int.
, vol.23
, pp. 465
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Swindell, C.S.1
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6
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33748226949
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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.
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(1994)
Angew. Chem. Int. Ed. Engl.
, vol.33
, pp. 15
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Nicolaou, K.C.1
Dai, W.2
Guy, R.3
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7
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0002502917
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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.
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(1994)
Contemporary Organic Synthesis
, pp. 47
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Boa, A.N.1
Jenkins, P.R.2
Lawrence, N.J.3
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9
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0028300090
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Nicolaou, K. C.; Caliborne, C.F.; Nantermet, P.G.; Couladouros, E.A.; Sorenson, E. J. J. Am. Chem. Soc. 1994, 116, 1591.
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(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 1591
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Nicolaou, K.C.1
Caliborne, C.F.2
Nantermet, P.G.3
Couladouros, E.A.4
Sorenson, E.J.5
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10
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0026505052
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a) Sonawane, H. R.; Nanjundiah, B. S.; Nazeruddin, G.M. Tetrahedron Lett. 1992, 33, 1645.
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Tetrahedron Lett.
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Sonawane, H.R.1
Nanjundiah, B.S.2
Nazeruddin, G.M.3
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11
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0026588915
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b) Ghosh, S.; Karpha, A.; Saha, G.; Patra, D. Tetrahedron Lett. 1992, 33, 2363.
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Tetrahedron Lett.
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Ghosh, S.1
Karpha, A.2
Saha, G.3
Patra, D.4
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14
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0001635506
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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.
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J. Am. Chem. Soc.
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Wender, P.A.1
Mucciaro, T.P.2
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15
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0028931514
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and referrences cited therein
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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.
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Tetrahedron Lett.
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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
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16
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85033747454
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note
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25= - 42°(neat)}a component of Indian turpentine oil.
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17
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84970605889
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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.
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(1981)
Helv.Chim.Acta
, vol.64
, pp. 943
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Escher, S.1
Giersch, W.2
Ohloff, G.3
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18
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85033753901
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note
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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%.
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19
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0001343749
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An analogus asymmetric transformation has been recently reported by Stork, G.; Hutchinson, D.; Okabe, M.; Parker, D.; Choon Sup Ra.; Ribereau, F.; Suzuki, T.; Zebovitz, T. Pure & Appl. Chem. 1992, 64, 1809:
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Pure & Appl. Chem.
, vol.64
, pp. 1809
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Stork, G.1
Hutchinson, D.2
Okabe, M.3
Parker, D.4
Ra, C.S.5
Ribereau, F.6
Suzuki, T.7
Zebovitz, T.8
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20
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85033757363
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note
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16O: C, 80.48; H, 9.76: Found: C, 80.36; H, 9.82.
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-
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21
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85033749827
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note
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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.
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22
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0028308309
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a) Seto, M.; Morihira, K.; Horiguchi, Y.; Kuwajima, I. J. Org. Chem. 1994, 59, 3165-3174.
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J. Org. Chem.
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Seto, M.1
Morihira, K.2
Horiguchi, Y.3
Kuwajima, I.4
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23
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0026780868
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b) Queneau, Y.; Krol, W. J.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 4043.
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J. Org. Chem.
, vol.57
, pp. 4043
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Queneau, Y.1
Krol, W.J.2
Bornmann, W.G.3
Danishefsky, S.J.4
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24
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85033754175
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note
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2: C,79.06; H,8.53. Found; C,79.28; H,8.42.
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