메뉴 건너뛰기




Volumn 100, Issue 9, 2000, Pages 3455-3482

Synthesis of strychnine

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ATOMS; CHEMICAL BONDS; CONFORMATIONS; ENZYMES; MOLECULAR STRUCTURE; REACTION KINETICS; SYNTHESIS (CHEMICAL); TOXICITY;

EID: 0034273688     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr9902547     Document Type: Article
Times cited : (294)

References (204)
  • 6
    • 0342638171 scopus 로고    scopus 로고
    • Creasey, W. A. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: New York, 1994; Supplement to Vol. 25, Part 4, pp 715-754.
    • Monoterpenoid Indole Alkaloids
    • Creasey, W.A.1
  • 7
    • 0342638169 scopus 로고
    • Taylor, E. C., Ed.; Wiley: New York
    • Creasey, W. A. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: New York, 1994; Supplement to Vol. 25, Part 4, pp 715-754.
    • (1994) The Chemistry of Heterocyclic Compounds , vol.25 , Issue.PART 4 , pp. 715-754
    • Saxton, J.E.1
  • 9
    • 0001828811 scopus 로고
    • Otterson, O. P., Storm-Mathisen, J. Eds.; Wiley: New York
    • Aprison, M. H. In Glycine Neurotransmision; Otterson, O. P., Storm-Mathisen, J. Eds.; Wiley: New York, 1990; pp 1-23.
    • (1990) Glycine Neurotransmision , pp. 1-23
    • Aprison, M.H.1
  • 12
    • 0343508472 scopus 로고
    • Regnault, V. Ann. 1838, 26, 17, 35.
    • (1838) Ann. , vol.26 , pp. 17
    • Regnault, V.1
  • 14
    • 37049168339 scopus 로고
    • The correct structure of strychnine first appeared in publications from Robinson's laboratory, although at that time his group favored a slightly different structure: Briggs, L. H.; Openshaw, H. T.; Robinson, R. J. Chem. Soc. 1946, 903-908. Holmes, H. L.; Openshaw, H. T.; Robinson, R. J. Chem. Soc. 1946, 910-912.
    • (1946) J. Chem. Soc. , pp. 903-908
    • Briggs, L.H.1    Openshaw, H.T.2    Robinson, R.3
  • 15
    • 37049153502 scopus 로고
    • The correct structure of strychnine first appeared in publications from Robinson's laboratory, although at that time his group favored a slightly different structure: Briggs, L. H.; Openshaw, H. T.; Robinson, R. J. Chem. Soc. 1946, 903-908. Holmes, H. L.; Openshaw, H. T.; Robinson, R. J. Chem. Soc. 1946, 910-912.
    • (1946) J. Chem. Soc. , pp. 910-912
    • Holmes, H.L.1    Openshaw, H.T.2    Robinson, R.3
  • 16
    • 77957037090 scopus 로고
    • Manske, R. H. F., Ed.; Academic Press: New York
    • Smith, G. F. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1965; Vol. 8, pp 591-671.
    • (1965) The Alkaloids , vol.8 , pp. 591-671
    • Smith, G.F.1
  • 20
    • 0000686657 scopus 로고
    • (c) Bokhoven, C.; Schoone, J. C.; Bijvoet, J. M. Acta Crystallogr. 1951, 4, 275-280. See also: Mostad, A. Acta Chem. Scand. 1985, 39B, 705-716.
    • (1985) Acta Chem. Scand. , vol.39 B , pp. 705-716
    • Mostad, A.1
  • 28
    • 0011833235 scopus 로고    scopus 로고
    • For reviews, see: (a) Sapi, J.; Massiot, G. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; In The Chemistry of Heterocyclic Compounds; Taylor E. C., Ed.; Wiley: New York, 1994; Supplement to Vol. 25, Part 4; pp 279-355.
    • Monoterpenoid Indole Alkaloids
    • Sapi, J.1    Massiot, G.2
  • 29
    • 0003540638 scopus 로고
    • Taylor E. C., Ed.; Wiley: New York
    • For reviews, see: (a) Sapi, J.; Massiot, G. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; In The Chemistry of Heterocyclic Compounds; Taylor E. C., Ed.; Wiley: New York, 1994; Supplement to Vol. 25, Part 4; pp 279-355.
    • (1994) The Chemistry of Heterocyclic Compounds , vol.25 , Issue.PART 4 , pp. 279-355
    • Saxton, J.E.1
  • 30
    • 1542499040 scopus 로고    scopus 로고
    • Cordell G. A., Ed.; Academic Press: New York
    • (b) Bosch, J.; Bonjoch, J.; Amat, M. In The Alkaloids; Cordell G. A., Ed.; Academic Press: New York, 1996; Vol. 48, pp 75-189.
    • (1996) The Alkaloids , vol.48 , pp. 75-189
    • Bosch, J.1    Bonjoch, J.2    Amat, M.3
  • 31
    • 0004812444 scopus 로고
    • Phillipson, J. D., Zenk, M. H., Eds.; Academic Press: London
    • For biogenetic aspects, see: (a) Bisset, N. G. In Indole and Biogenertically Related Alkaloids; Phillipson, J. D., Zenk, M. H., Eds.; Academic Press: London, 1980; pp 27-61.
    • (1980) Indole and Biogenertically Related Alkaloids , pp. 27-61
    • Bisset, N.G.1
  • 36
    • 0343508471 scopus 로고    scopus 로고
    • note
    • Strychnidine is the Chemical Abstracts' stereoparent used for strychnine derivatives; therefore, strychnine is 10-oxostrychnidine, see Figure 1.
  • 49
    • 0343072407 scopus 로고    scopus 로고
    • personal communication
    • (a) Martin, S. F., personal communication 1999.
    • (1999)
    • Martin, S.F.1
  • 51
    • 0343944171 scopus 로고    scopus 로고
    • note
    • In fact, Woodward and Magnus syntheses also achieved (-)-strychnine since they used relay compounds, prepared from natural strychnine, for the last synthetic steps.
  • 56
    • 37049048949 scopus 로고
    • For other procedures for the degradation of strychnine into the Wieland-Gumlich aldehyde, see: (a) Anet, F. A. L.; Robinson, R. J. Chem. Soc. 1955, 2253-2262.
    • (1955) J. Chem. Soc. , pp. 2253-2262
    • Anet, F.A.L.1    Robinson, R.2
  • 59
    • 0342638166 scopus 로고
    • (c) Szabo, L.; Clauder, O. Acta Chim. Acad. Sci. Hung. 1977, 95, 85-100; Chem. Abstr. 1978, 89, 43889.
    • (1978) Chem. Abstr. , vol.89 , pp. 43889
  • 62
    • 84942716182 scopus 로고
    • Although indirectly, the conversion of the Wieland-Gumlich aldehyde into strychnine had been achieved earlier: Robinson, R.; Saxton, J. E. J. Chem. Soc. 1952, 982-986.
    • (1952) J. Chem. Soc. , pp. 982-986
    • Robinson, R.1    Saxton, J.E.2
  • 64
  • 65
    • 0343508466 scopus 로고    scopus 로고
    • note
    • Although it cannot be said for certain that 11 possesses the relative configuration represented, it seems likely that steric factors would favor the process leading to the formation of the diastereomer shown.
  • 68
    • 0002130345 scopus 로고
    • The conversion of simple acids to methyl ketones under similar conditions were known at that time. See, for example: King, J. A.; McMillan, F. H. J. Am. Chem. Soc. 1951, 73, 4911-4915. King, J. A.; McMillan, F. H. J. Am. Chem. Soc. 1955, 77, 2814-2816.
    • (1951) J. Am. Chem. Soc. , vol.73 , pp. 4911-4915
    • King, J.A.1    McMillan, F.H.2
  • 69
    • 33947469986 scopus 로고
    • The conversion of simple acids to methyl ketones under similar conditions were known at that time. See, for example: King, J. A.; McMillan, F. H. J. Am. Chem. Soc. 1951, 73, 4911-4915. King, J. A.; McMillan, F. H. J. Am. Chem. Soc. 1955, 77, 2814-2816.
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 2814-2816
    • King, J.A.1    McMillan, F.H.2
  • 70
    • 0343508465 scopus 로고    scopus 로고
    • note
    • An alternative bimolecular (intermolecular) pathway for this reaction cannot be ruled out.
  • 75
    • 84984086724 scopus 로고
    • This catalytic aerial oxidation had been previously described by Schumann and Schmid from the same product obtained from natural sources by degradation. Schumann, D.; Schmid, H. Helv. Chim. Acta 1963, 46, 1996-2003.
    • (1963) Helv. Chim. Acta , vol.46 , pp. 1996-2003
    • Schumann, D.1    Schmid, H.2
  • 77
    • 0013601608 scopus 로고    scopus 로고
    • Beginning with the pioneering work of Dolby and Sakai in 1964, a number of procedures have been reported for the cleavage of the zero bridged single bond in tetra-or pentacyclic indole compounds incorporating a tetrahydro-β-carboline. For extensive references in this field, see: Bonjoch, J.; Fernàndez, J.-C.; Valls, N. J. Org. Chem. 1998, 63, 7338-7347.
    • (1998) J. Org. Chem. , vol.63 , pp. 7338-7347
    • Bonjoch, J.1    Fernàndez, J.-C.2    Valls, N.3
  • 78
    • 0016810389 scopus 로고
    • For other synthetic entries to stemmadenine derivatives, see: (a) Wu, A.; Snieckus, V. Tetrahedron Lett. 1975, 2057-2060.
    • (1975) Tetrahedron Lett. , pp. 2057-2060
    • Wu, A.1    Snieckus, V.2
  • 81
    • 33947478289 scopus 로고
    • For mercuric acetate-promoted oxidative cyclization of nitrogen-containing rings upon indoles, see inter alia: (a) Wenkert, E.; Wickberg, B. J. Am. Chem. Soc. 1962, 84, 4914-1919.
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 4914-11919
    • Wenkert, E.1    Wickberg, B.2
  • 85
    • 0002038735 scopus 로고
    • Atta-ur-Rahman, Ed.; Elsevier: Amsterdam
    • It is interesting to note that the regioselectivity of the oxidative cyclization of related stemmadenine derivatives depends on the substituents and the reaction conditions, see: Bosch, J.; Bonjoch, J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, pp 31-88.
    • (1988) Studies in Natural Products Chemistry , vol.1 , pp. 31-88
    • Bosch, J.1    Bonjoch, J.2
  • 90
    • 0343508464 scopus 로고    scopus 로고
    • note
    • Earlier investigations in the Strychnos alkaloid synthesis made evident that only compounds with a cis relationship between the iminium salt and the C-C double bond can undergo the [3,3] sigmatropic rearrangement; see ref 53.
  • 100
    • 85027871817 scopus 로고
    • Deardorff, D. R.; Matthews, A. J.; McMeekin, D. S.; Craney, C. L. Tetrahedron Lett. 1986, 27, 1255-1256. Deardorff, D. R.; Windham, C. Q.; Craney, C. L. Org. Synth. 1995, 73, 25-35.
    • (1995) Org. Synth. , vol.73 , pp. 25-35
    • Deardorff, D.R.1    Windham, C.Q.2    Craney, C.L.3
  • 102
    • 0011163195 scopus 로고
    • The same sequence had previously been used by Overman for the introduction of the (E)-2-butenyl chain in an earlier investigation in the Strychnos alkaloid area: Overman, L. E.; Angle, S. R. J. Org. Chem. 1985, 50, 4021-4028.
    • (1985) J. Org. Chem. , vol.50 , pp. 4021-4028
    • Overman, L.E.1    Angle, S.R.2
  • 103
    • 0042869554 scopus 로고
    • For a review about the TIPS group, see: Rücker, C. Chem. Rev. 1995, 95, 1009-1064.
    • (1995) Chem. Rev. , vol.95 , pp. 1009-1064
    • Rücker, C.1
  • 104
    • 0343508463 scopus 로고    scopus 로고
    • note
    • 67 to protect both hydrogens of the aniline moiety.
  • 107
    • 77957095647 scopus 로고
    • Brossi A., Suffness, M., Eds.; Academic Press: New York
    • For the synthesis of other monoterpenoid indole alkaloid types, see inter alia: (a) Kuehne M. E.; Markó, I. In The Alkaloids; Brossi A., Suffness, M., Eds.; Academic Press: New York, 1990; Vol. 37, pp 77-131.
    • (1990) The Alkaloids , vol.37 , pp. 77-131
    • Kuehne, M.E.1    Markó, I.2
  • 114
    • 0029818921 scopus 로고    scopus 로고
    • Kuehne, M. E.; Wang, T.; Seraphin, D. Synlett 1995, 557-558. Kuehne, M. E.; Wang, T.; Seraphin, D. J. Org. Chem. 1996, 61, 7873-7881.
    • (1995) Synlett , pp. 557-558
    • Kuehne, M.E.1    Wang, T.2    Seraphin, D.3
  • 115
  • 120
    • 0342638159 scopus 로고    scopus 로고
    • note
    • b and the electrophilic substituent on carbon C-14: see ref 64.
  • 122
    • 33745498476 scopus 로고
    • The β-elimination to give the C12-C13 double bond instead of the conjugated isomer had been precedented for related compounds in the context of biogenetic studies of strychnine. Baser, K. H. C.; Bisset, N. G.; Hylands, P. J. Phytochemistry 1979, 18, 512-514.
    • (1979) Phytochemistry , vol.18 , pp. 512-514
    • Baser, K.H.C.1    Bisset, N.G.2    Hylands, P.J.3
  • 127
    • 0018223055 scopus 로고
    • The intermolecular addition of carbon nucleophiles at C-2 of chloroindolenines and the subsequent rearrangement of the resulting adduct has been precedented: Kuehne, M. E.; Hafter, R. J. Org. Chem. 1978, 43, 3702-3704. For a carbon-based nucleophilic addition to C-2 unsubstituted chloroindolenines, see: (a) Reference 77. (b) Schkeryantz, J. M.; Woo, J. C. G.; Siliphaivanh, P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 11964-11975.
    • (1978) J. Org. Chem. , vol.43 , pp. 3702-3704
    • Kuehne, M.E.1    Hafter, R.2
  • 128
    • 0033616118 scopus 로고    scopus 로고
    • The intermolecular addition of carbon nucleophiles at C-2 of chloroindolenines and the subsequent rearrangement of the resulting adduct has been precedented: Kuehne, M. E.; Hafter, R. J. Org. Chem. 1978, 43, 3702-3704. For a carbon-based nucleophilic addition to C-2 unsubstituted chloroindolenines, see: (a) Reference 77. (b) Schkeryantz, J. M.; Woo, J. C. G.; Siliphaivanh, P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 11964-11975.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 11964-11975
    • Schkeryantz, J.M.1    Woo, J.C.G.2    Siliphaivanh, P.3    Depew, K.M.4    Danishefsky, S.J.5
  • 129
    • 85077854948 scopus 로고
    • For a review, see: Krapcho, A. P. Synthesis 1982, 805-822, 893-914.
    • (1982) Synthesis , pp. 805-822
    • Krapcho, A.P.1
  • 130
    • 37049099381 scopus 로고
    • Displacement of the double bond from position C2-C16 in 106 to C16-C15 in 105 makes use of conditions similar to those developed for the synthesis of vindoline: (a) Danieli, B. Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Chem. Commun. 1984, 909-911.
    • (1984) J. Chem. Soc., Chem. Commun. , pp. 909-911
    • Danieli, B.1    Lesma, G.2    Palmisano, G.3    Riva, R.4
  • 133
    • 0000633011 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: New York
    • For a review, see: Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1992; Vol. 4 pp 833-863.
    • (1992) Comprehensive Organic Synthesis , vol.4 , pp. 833-863
    • Heck, R.F.1
  • 136
    • 0032192164 scopus 로고    scopus 로고
    • For the use of the intramolecular Heck reaction in the synthesis of indole alkaloids with an ethylidene side chain other than those of the Strychnos family, see: Birman, V. B.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 7219-7222. Birman, V. B.; Rawal, V. H. J. Org. Chem. 1998, 63, 9146-9147.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7219-7222
    • Birman, V.B.1    Rawal, V.H.2
  • 137
    • 0032509487 scopus 로고    scopus 로고
    • For the use of the intramolecular Heck reaction in the synthesis of indole alkaloids with an ethylidene side chain other than those of the Strychnos family, see: Birman, V. B.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 7219-7222. Birman, V. B.; Rawal, V. H. J. Org. Chem. 1998, 63, 9146-9147.
    • (1998) J. Org. Chem. , vol.63 , pp. 9146-9147
    • Birman, V.B.1    Rawal, V.H.2
  • 138
  • 142
    • 0000733389 scopus 로고
    • For an unexpected Heck reaction on a related carbamate derivative, see: Rawal, V. H.; Michoud, C. J. Org. Chem. 1993, 58, 5583-5584.
    • (1993) J. Org. Chem. , vol.58 , pp. 5583-5584
    • Rawal, V.H.1    Michoud, C.2
  • 146
    • 0020383091 scopus 로고
    • For the use of 2-nitrophenyl derivatives as precursors of the indoline nucleus in alkaloid synthesis, see inter alia: Takano, S.; Goto, E.; Hirama, M.; Ogasawara, K. Chem. Pharm. Bull. 1982, 30, 2641-2643. Heathcock, C. H.; Norman, M. H.; Dickman, D. A.; J. Org. Chem. 1990, 55, 798-811. Mittendorf, J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1990, 46, 4049-4062. Padwa, A.; Harring, S. R.; Semones, M. A. J. Org. Chem. 1998, 63, 44-54. Kozmin, S. A.; Rawal, V. H. J. Am Chem. Soc. 1998, 120, 13523-13524.
    • (1982) Chem. Pharm. Bull. , vol.30 , pp. 2641-2643
    • Takano, S.1    Goto, E.2    Hirama, M.3    Ogasawara, K.4
  • 147
    • 0025265859 scopus 로고
    • For the use of 2-nitrophenyl derivatives as precursors of the indoline nucleus in alkaloid synthesis, see inter alia: Takano, S.; Goto, E.; Hirama, M.; Ogasawara, K. Chem. Pharm. Bull. 1982, 30, 2641-2643. Heathcock, C. H.; Norman, M. H.; Dickman, D. A.; J. Org. Chem. 1990, 55, 798-811. Mittendorf, J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1990, 46, 4049-4062. Padwa, A.; Harring, S. R.; Semones, M. A. J. Org. Chem. 1998, 63, 44-54. Kozmin, S. A.; Rawal, V. H. J. Am Chem. Soc. 1998, 120, 13523-13524.
    • (1990) J. Org. Chem. , vol.55 , pp. 798-811
    • Heathcock, C.H.1    Norman, M.H.2    Dickman, D.A.3
  • 148
    • 0001274215 scopus 로고
    • For the use of 2-nitrophenyl derivatives as precursors of the indoline nucleus in alkaloid synthesis, see inter alia: Takano, S.; Goto, E.; Hirama, M.; Ogasawara, K. Chem. Pharm. Bull. 1982, 30, 2641-2643. Heathcock, C. H.; Norman, M. H.; Dickman, D. A.; J. Org. Chem. 1990, 55, 798-811. Mittendorf, J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1990, 46, 4049-4062. Padwa, A.; Harring, S. R.; Semones, M. A. J. Org. Chem. 1998, 63, 44-54. Kozmin, S. A.; Rawal, V. H. J. Am Chem. Soc. 1998, 120, 13523-13524.
    • (1990) Tetrahedron , vol.46 , pp. 4049-4062
    • Mittendorf, J.1    Hiemstra, H.2    Speckamp, W.N.3
  • 149
    • 0002254975 scopus 로고    scopus 로고
    • For the use of 2-nitrophenyl derivatives as precursors of the indoline nucleus in alkaloid synthesis, see inter alia: Takano, S.; Goto, E.; Hirama, M.; Ogasawara, K. Chem. Pharm. Bull. 1982, 30, 2641-2643. Heathcock, C. H.; Norman, M. H.; Dickman, D. A.; J. Org. Chem. 1990, 55, 798-811. Mittendorf, J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1990, 46, 4049-4062. Padwa, A.; Harring, S. R.; Semones, M. A. J. Org. Chem. 1998, 63, 44-54. Kozmin, S. A.; Rawal, V. H. J. Am Chem. Soc. 1998, 120, 13523-13524.
    • (1998) J. Org. Chem. , vol.63 , pp. 44-54
    • Padwa, A.1    Harring, S.R.2    Semones, M.A.3
  • 150
    • 0032583442 scopus 로고    scopus 로고
    • For the use of 2-nitrophenyl derivatives as precursors of the indoline nucleus in alkaloid synthesis, see inter alia: Takano, S.; Goto, E.; Hirama, M.; Ogasawara, K. Chem. Pharm. Bull. 1982, 30, 2641-2643. Heathcock, C. H.; Norman, M. H.; Dickman, D. A.; J. Org. Chem. 1990, 55, 798-811. Mittendorf, J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1990, 46, 4049-4062. Padwa, A.; Harring, S. R.; Semones, M. A. J. Org. Chem. 1998, 63, 44-54. Kozmin, S. A.; Rawal, V. H. J. Am Chem. Soc. 1998, 120, 13523-13524.
    • (1998) J. Am Chem. Soc. , vol.120 , pp. 13523-13524
    • Kozmin, S.A.1    Rawal, V.H.2
  • 153
    • 0343072399 scopus 로고    scopus 로고
    • (c) See also ref 83
    • (c) See also ref 83.
  • 160
    • 0342638158 scopus 로고    scopus 로고
    • note
    • This alkylating agent was prepared following the Rawal protocol, see ref 26.
  • 161
    • 0343508438 scopus 로고    scopus 로고
    • note
    • 2Me group at C-16, other quenchers were studied: lithium cyanide to introduce a CN group, methyl acrylate to introduce a three-carbon substituent, and vinyltributyltin to introduce a vinyl group.
  • 162
    • 0343508461 scopus 로고    scopus 로고
    • note
    • 110
  • 167
    • 0027982628 scopus 로고
    • 22b for the methoxycarbonylation of azatricyclic derivative 58, which differs from 131 in the substituent on the aromatic ring. This fact suggets that the nitro group is the cause of the different behavior. For an unusual reaction of a related nitro ketone under basic conditions, see: Solé, D.; Parés, A.; Bonjoch, J. Tetrahedron 1994, 50, 9769-9774.
    • (1994) Tetrahedron , vol.50 , pp. 9769-9774
    • Solé, D.1    Parés, A.2    Bonjoch, J.3
  • 168
    • 0000373038 scopus 로고
    • For the biogenetic Corynanthe-Strychnos relationship, see: (a) Wenkert, E.; Wickberg, B. J. Am. Chem. Soc. 1965, 87, 1580-1589.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 1580-1589
    • Wenkert, E.1    Wickberg, B.2
  • 171
    • 0343072376 scopus 로고    scopus 로고
    • (d) see refs 16 and 17
    • (d) see refs 16 and 17.
  • 175
    • 0023134868 scopus 로고
    • See also ref 84
    • A related rearrangement had previously been used in the synthesis of the Aspidosperma alkaloid (-)-vindoline, see: Feldman, P. L.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 1603-1604. See also ref 84.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 1603-1604
    • Feldman, P.L.1    Rapoport, H.2
  • 203
    • 0343072370 scopus 로고    scopus 로고
    • See pages 336-337 in ref 15a
    • See pages 336-337 in ref 15a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.