메뉴 건너뛰기




Volumn , Issue 19, 2002, Pages 3315-3325

Total synthesis of (+)-pumiliotoxin 251D

Author keywords

Aldol reactions; Alkaloids; Lactams; Olefinations; Total synthesis

Indexed keywords

ALKENE; AMIDE; INDOLIZIDINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PUMILIOTOXIN;

EID: 0036795058     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200210)2002:19<3315::AID-EJOC3315>3.0.CO;2-2     Document Type: Article
Times cited : (40)

References (60)
  • 1
    • 0001098602 scopus 로고    scopus 로고
    • [1a] Review on total synthesis of pumiliotoxins: L. E. Overman, A. S. Franklin, Chem. Rev. 1996, 96, 505-522. [1b] Further ref.: B. M. Trost, T. S. Scanlan, J. Am. Chem. Soc. 1989, 111, 4988-4990.
    • (1996) Chem. Rev. , vol.96 , pp. 505-522
    • Overman, L.E.1    Franklin, A.S.2
  • 2
    • 0000525149 scopus 로고
    • [1a] Review on total synthesis of pumiliotoxins: L. E. Overman, A. S. Franklin, Chem. Rev. 1996, 96, 505-522. [1b] Further ref.: B. M. Trost, T. S. Scanlan, J. Am. Chem. Soc. 1989, 111, 4988-4990.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 4988-4990
    • Trost, B.M.1    Scanlan, T.S.2
  • 3
    • 0011838270 scopus 로고
    • For recent reviews, see: [2a] J. W. Daly, H. M. Garraffo, T. F. Spande, Alkaloids 1993, 43, 185-288. [2b] J. W. Daly, H. M. Garaffo, T. F. Spande, in: Alkaloids: Chemical and Biological Perspectives: Vol. 13 (Ed.: S. W. Pelletier), Elsevier Science Ltd.: Oxford, 1999; pp. 1-161.
    • (1993) Alkaloids , vol.43 , pp. 185-288
    • Daly, J.W.1    Garraffo, H.M.2    Spande, T.F.3
  • 4
    • 11144349848 scopus 로고    scopus 로고
    • Ed.: S.W. Pelletier), Elsevier Science Ltd.: Oxford
    • For recent reviews, see: [2a] J. W. Daly, H. M. Garraffo, T. F. Spande, Alkaloids 1993, 43, 185-288. [2b] J. W. Daly, H. M. Garaffo, T. F. Spande, in: Alkaloids: Chemical and Biological Perspectives: Vol. 13 (Ed.: S. W. Pelletier), Elsevier Science Ltd.: Oxford, 1999; pp. 1-161.
    • (1999) Alkaloids: Chemical and Biological Perspectives , vol.13 , pp. 1-161
    • Daly, J.W.1    Garaffo, H.M.2    Spande, T.F.3
  • 13
    • 0000373985 scopus 로고
    • [7a] D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy, T. Gallagher, J. Am. Chem. Soc. 1991, 113, 2652-2656. [7b] A. G. M. Barrett, F. Damiani, J. Org. Chem. 1999, 64, 1410-1411. [7c] Y. Ni, G. Zhao, Y. Ding, J. Chem. Soc., Perkin Trans. 1 2000, 3264-3266. [7d] S. F. Martin, S. K. Bur, Tetrahedron 1999, 55, 8905-8914. For a related application in the allo-pumiliotoxin series see: [7e] allo-ptx 339 B′: S. W. Goldstein, L. E. Overman, M. H. Rabinowitz, J. Org. Chem. 1992, 57, 1179-1190. [7f] allo-px 323B′: C.-H. Tan, A. B. Holmes, Chem. Eur. J. 2001, 7, 1845-1854.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 2652-2656
    • Fox, D.N.A.1    Lathbury, D.2    Mahon, M.F.3    Molloy, K.C.4    Gallagher, T.5
  • 14
    • 0033582566 scopus 로고    scopus 로고
    • [7a] D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy, T. Gallagher, J. Am. Chem. Soc. 1991, 113, 2652-2656. [7b] A. G. M. Barrett, F. Damiani, J. Org. Chem. 1999, 64, 1410-1411. [7c] Y. Ni, G. Zhao, Y. Ding, J. Chem. Soc., Perkin Trans. 1 2000, 3264-3266. [7d] S. F. Martin, S. K. Bur, Tetrahedron 1999, 55, 8905-8914. For a related application in the allo-pumiliotoxin series see: [7e] allo-ptx 339 B′: S. W. Goldstein, L. E. Overman, M. H. Rabinowitz, J. Org. Chem. 1992, 57, 1179-1190. [7f] allo-px 323B′: C.-H. Tan, A. B. Holmes, Chem. Eur. J. 2001, 7, 1845-1854.
    • (1999) J. Org. Chem. , vol.64 , pp. 1410-1411
    • Barrett, A.G.M.1    Damiani, F.2
  • 15
    • 0034619270 scopus 로고    scopus 로고
    • [7a] D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy, T. Gallagher, J. Am. Chem. Soc. 1991, 113, 2652-2656. [7b] A. G. M. Barrett, F. Damiani, J. Org. Chem. 1999, 64, 1410-1411. [7c] Y. Ni, G. Zhao, Y. Ding, J. Chem. Soc., Perkin Trans. 1 2000, 3264-3266. [7d] S. F. Martin, S. K. Bur, Tetrahedron 1999, 55, 8905-8914. For a related application in the allo-pumiliotoxin series see: [7e] allo-ptx 339 B′: S. W. Goldstein, L. E. Overman, M. H. Rabinowitz, J. Org. Chem. 1992, 57, 1179-1190. [7f] allo-px 323B′: C.-H. Tan, A. B. Holmes, Chem. Eur. J. 2001, 7, 1845-1854.
    • (2000) J. Chem. Soc., Perkin Trans. 1. , pp. 3264-3266
    • Ni, Y.1    Zhao, G.2    Ding, Y.3
  • 16
    • 0033575493 scopus 로고    scopus 로고
    • [7a] D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy, T. Gallagher, J. Am. Chem. Soc. 1991, 113, 2652-2656. [7b] A. G. M. Barrett, F. Damiani, J. Org. Chem. 1999, 64, 1410-1411. [7c] Y. Ni, G. Zhao, Y. Ding, J. Chem. Soc., Perkin Trans. 1 2000, 3264-3266. [7d] S. F. Martin, S. K. Bur, Tetrahedron 1999, 55, 8905-8914. For a related application in the allo-pumiliotoxin series see: [7e] allo-ptx 339 B′: S. W. Goldstein, L. E. Overman, M. H. Rabinowitz, J. Org. Chem. 1992, 57, 1179-1190. [7f] allo-px 323B′: C.-H. Tan, A. B. Holmes, Chem. Eur. J. 2001, 7, 1845-1854.
    • (1999) Tetrahedron , vol.55 , pp. 8905-8914
    • Martin, S.F.1    Bur, S.K.2
  • 17
    • 0001608555 scopus 로고
    • [7a] D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy, T. Gallagher, J. Am. Chem. Soc. 1991, 113, 2652-2656. [7b] A. G. M. Barrett, F. Damiani, J. Org. Chem. 1999, 64, 1410-1411. [7c] Y. Ni, G. Zhao, Y. Ding, J. Chem. Soc., Perkin Trans. 1 2000, 3264-3266. [7d] S. F. Martin, S. K. Bur, Tetrahedron 1999, 55, 8905-8914. For a related application in the allo-pumiliotoxin series see: [7e] allo-ptx 339 B′: S. W. Goldstein, L. E. Overman, M. H. Rabinowitz, J. Org. Chem. 1992, 57, 1179-1190. [7f] allo-px 323B′: C.-H. Tan, A. B. Holmes, Chem. Eur. J. 2001, 7, 1845-1854.
    • (1992) J. Org. Chem. , vol.57 , pp. 1179-1190
    • Goldstein, S.W.1    Overman, L.E.2    Rabinowitz, M.H.3
  • 18
    • 0035805339 scopus 로고    scopus 로고
    • [7a] D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy, T. Gallagher, J. Am. Chem. Soc. 1991, 113, 2652-2656. [7b] A. G. M. Barrett, F. Damiani, J. Org. Chem. 1999, 64, 1410-1411. [7c] Y. Ni, G. Zhao, Y. Ding, J. Chem. Soc., Perkin Trans. 1 2000, 3264-3266. [7d] S. F. Martin, S. K. Bur, Tetrahedron 1999, 55, 8905-8914. For a related application in the allo-pumiliotoxin series see: [7e] allo-ptx 339 B′: S. W. Goldstein, L. E. Overman, M. H. Rabinowitz, J. Org. Chem. 1992, 57, 1179-1190. [7f] allo-px 323B′: C.-H. Tan, A. B. Holmes, Chem. Eur. J. 2001, 7, 1845-1854.
    • (2001) Chem. Eur. J. , vol.7 , pp. 1845-1854
    • Tan, C.-H.1    Holmes, A.B.2
  • 22
    • 0023855168 scopus 로고
    • [9a] Synthesis of ptx A and B: L. E. Overman, M. J. Sharp, Tetrahedron Lett. 1988, 29, 901-904. [9b] Synthesis of allo-ptx 339A: L. E. Overman, L. A. Robinson, J. Zablocki, J. Am. Chem. Soc. 1992, 114, 368-369. [9c] Synthesis of ptx-267A, 323 B′ and 339A: C. Caderas, R. Lett, L. E. Overman, M. H. Rabinowitz, L. A. Robinson, M. J. Sharp, J. Zablocki, J. Am. Chem. Soc. 1996, 118 1996,118, 9073-9082. [9d] T M. Bargar, R. M. Lett, P. L. Johnson, J. E. Hunter, C. P. Chang, D. J. Pernich, M. R. Sabol, M. R. Dick, J. Agric. Food Chem. 1995, 43, 1044-1051.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 901-904
    • Overman, L.E.1    Sharp, M.J.2
  • 23
    • 0026593160 scopus 로고
    • [9a] Synthesis of ptx A and B: L. E. Overman, M. J. Sharp, Tetrahedron Lett. 1988, 29, 901-904. [9b] Synthesis of allo-ptx 339A: L. E. Overman, L. A. Robinson, J. Zablocki, J. Am. Chem. Soc. 1992, 114, 368-369. [9c] Synthesis of ptx-267A, 323 B′ and 339A: C. Caderas, R. Lett, L. E. Overman, M. H. Rabinowitz, L. A. Robinson, M. J. Sharp, J. Zablocki, J. Am. Chem. Soc. 1996, 118 1996,118, 9073-9082. [9d] T M. Bargar, R. M. Lett, P. L. Johnson, J. E. Hunter, C. P. Chang, D. J. Pernich, M. R. Sabol, M. R. Dick, J. Agric. Food Chem. 1995, 43, 1044-1051.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 368-369
    • Overman, L.E.1    Robinson, L.A.2    Zablocki, J.3
  • 24
    • 10244222753 scopus 로고    scopus 로고
    • [9a] Synthesis of ptx A and B: L. E. Overman, M. J. Sharp, Tetrahedron Lett. 1988, 29, 901-904. [9b] Synthesis of allo-ptx 339A: L. E. Overman, L. A. Robinson, J. Zablocki, J. Am. Chem. Soc. 1992, 114, 368-369. [9c] Synthesis of ptx-267A, 323 B′ and 339A: C. Caderas, R. Lett, L. E. Overman, M. H. Rabinowitz, L. A. Robinson, M. J. Sharp, J. Zablocki, J. Am. Chem. Soc. 1996, 118 1996,118, 9073-9082. [9d] T M. Bargar, R. M. Lett, P. L. Johnson, J. E. Hunter, C. P. Chang, D. J. Pernich, M. R. Sabol, M. R. Dick, J. Agric. Food Chem. 1995, 43, 1044-1051.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9073-9082
    • Caderas, C.1    Lett, R.2    Overman, L.E.3    Rabinowitz, M.H.4    Robinson, L.A.5    Sharp, M.J.6    Zablocki, J.7
  • 25
    • 0001080206 scopus 로고
    • [9a] Synthesis of ptx A and B: L. E. Overman, M. J. Sharp, Tetrahedron Lett. 1988, 29, 901-904. [9b] Synthesis of allo-ptx 339A: L. E. Overman, L. A. Robinson, J. Zablocki, J. Am. Chem. Soc. 1992, 114, 368-369. [9c] Synthesis of ptx-267A, 323 B′ and 339A: C. Caderas, R. Lett, L. E. Overman, M. H. Rabinowitz, L. A. Robinson, M. J. Sharp, J. Zablocki, J. Am. Chem. Soc. 1996, 118 1996,118, 9073-9082. [9d] T M. Bargar, R. M. Lett, P. L. Johnson, J. E. Hunter, C. P. Chang, D. J. Pernich, M. R. Sabol, M. R. Dick, J. Agric. Food Chem. 1995, 43, 1044-1051.
    • (1995) J. Agric. Food Chem. , vol.43 , pp. 1044-1051
    • Bargar, T.M.1    Lett, R.M.2    Johnson, P.L.3    Hunter, J.E.4    Chang, C.P.5    Pernich, D.J.6    Sabol, M.R.7    Dick, M.R.8
  • 28
    • 33646066450 scopus 로고
    • for stereoselective Z Horner olefinations see: [12a] W. C. Still, C. Gennari, Tetrahedron Lett. 1983, 24, 4405-4408. [12b] K. Ando, J. Org. Chem. 1997, 62, 1934-1939. [12c] K. Ando, J. Org. Chem. 1998, 63, 8411-8416
    • (1983) Tetrahedron Lett. , vol.24 , pp. 4405-4408
    • Still, W.C.1    Gennari, C.2
  • 29
    • 0000262852 scopus 로고    scopus 로고
    • for stereoselective Z Horner olefinations see: [12a] W. C. Still, C. Gennari, Tetrahedron Lett. 1983, 24, 4405-4408. [12b] K. Ando, J. Org. Chem. 1997, 62, 1934-1939. [12c] K. Ando, J. Org. Chem. 1998, 63, 8411-8416
    • (1997) J. Org. Chem. , vol.62 , pp. 1934-1939
    • Ando, K.1
  • 30
    • 0032514965 scopus 로고    scopus 로고
    • for stereoselective Z Horner olefinations see: [12a] W. C. Still, C. Gennari, Tetrahedron Lett. 1983, 24, 4405-4408. [12b] K. Ando, J. Org. Chem. 1997, 62, 1934-1939. [12c] K. Ando, J. Org. Chem. 1998, 63, 8411-8416
    • (1998) J. Org. Chem. , vol.63 , pp. 8411-8416
    • Ando, K.1
  • 31
    • 0010833171 scopus 로고    scopus 로고
    • See ref. [9c]
    • [13a] See ref. [9c]
  • 39
    • 0010898234 scopus 로고    scopus 로고
    • note
    • For preparation procedures and spectroscopic data see supporting information.
  • 40
    • 0010944001 scopus 로고    scopus 로고
    • note
    • The reaction of the hexanal and the core indolizidinone yielded a small amount of a third diastereomer, but the configuration of the new stereogenic centers were not established. For preparation procedures and spectroscopic data see supporting information.
  • 42
    • 0033550193 scopus 로고    scopus 로고
    • For reviews on phosphonate syntheses see: [19a] F. Eymery, B. Iorga, P. Savignac, Tetrahedron 1999, 55, 13109-13150. [19b] D. F. Wiemer, Tetrahedron 1997, 53, 16609-16644.
    • (1999) Tetrahedron , vol.55 , pp. 13109-13150
    • Eymery, F.1    Iorga, B.2    Savignac, P.3
  • 43
    • 0030810309 scopus 로고    scopus 로고
    • For reviews on phosphonate syntheses see: [19a] F. Eymery, B. Iorga, P. Savignac, Tetrahedron 1999, 55, 13109-13150. [19b] D. F. Wiemer, Tetrahedron 1997, 53, 16609-16644.
    • (1997) Tetrahedron , vol.53 , pp. 16609-16644
    • Wiemer, D.F.1
  • 50
    • 0010833173 scopus 로고    scopus 로고
    • note
    • For detailed data see supporting information.
  • 53
    • 84989478646 scopus 로고
    • Representative reference for oxidation: [25a] A. J. Mancuso, D. Swern, Synthesis 1981, 165-196. [25b] R. H. Mueller, M. E. Thompson, R. M. DiPardo, J. Org. Chem. 1984, 49, 2217-2231. [25c] S. Ribe, P. Wipf, Chem. Commun. 2001, 299-307.
    • (1981) Synthesis , pp. 165-196
    • Mancuso, A.J.1    Swern, D.2
  • 54
    • 0001078504 scopus 로고
    • Representative reference for oxidation: [25a] A. J. Mancuso, D. Swern, Synthesis 1981, 165-196. [25b] R. H. Mueller, M. E. Thompson, R. M. DiPardo, J. Org. Chem. 1984, 49, 2217-2231. [25c] S. Ribe, P. Wipf, Chem. Commun. 2001, 299-307.
    • (1984) J. Org. Chem. , vol.49 , pp. 2217-2231
    • Mueller, R.H.1    Thompson, M.E.2    DiPardo, R.M.3
  • 55
    • 0035925228 scopus 로고    scopus 로고
    • Representative reference for oxidation: [25a] A. J. Mancuso, D. Swern, Synthesis 1981, 165-196. [25b] R. H. Mueller, M. E. Thompson, R. M. DiPardo, J. Org. Chem. 1984, 49, 2217-2231. [25c] S. Ribe, P. Wipf, Chem. Commun. 2001, 299-307.
    • (2001) Chem. Commun. , pp. 299-307
    • Ribe, S.1    Wipf, P.2
  • 56
    • 0010893226 scopus 로고    scopus 로고
    • note
    • 1 (Figure 2).
  • 57
  • 58
    • 0010898235 scopus 로고    scopus 로고
    • note
    • 1H-HMQC, and H,H-COSY spectra.
  • 59
    • 0010831996 scopus 로고    scopus 로고
    • note
    • 3, no grainy suspension but a sticky precipitate was formed (no stirring possible), the reduction failed.
  • 60
    • 0010948068 scopus 로고    scopus 로고
    • note
    • The HPLC behavior of PTX 251 D 28 strongly depends on the injected concentration, the product was purified considering its tendency of a decreasing retention time when the column was overloaded.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.