메뉴 건너뛰기




Volumn 62, Issue 2, 1997, Pages 377-386

Total synthesis of (+)-aspicilin. The naked carbon skeleton strategy vs the bioorganic approach

Author keywords

[No Author keywords available]

Indexed keywords

ASPERLICIN; MACROLIDE;

EID: 0031038956     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9614811     Document Type: Article
Times cited : (43)

References (33)
  • 5
    • 0003129117 scopus 로고
    • Scheffold, R., Ed.; Salle & Sauerländer: Frankfurt/Aarau
    • Seebach, D.; Hungerbühler, E. In Modern Synthetic Methods; Scheffold, R., Ed.; Salle & Sauerländer: Frankfurt/Aarau, 1980; Vol. 2, p 91.
    • (1980) Modern Synthetic Methods , vol.2 , pp. 91
    • Seebach, D.1    Hungerbühler, E.2
  • 8
    • 0002578608 scopus 로고
    • Ojima, I., Ed.; VCH Publishers Inc.: New York
    • Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.: New York, 1993; pp 159-202.
    • (1993) Catalytic Asymmetric Synthesis , pp. 159-202
    • Jacobsen, E.N.1
  • 12
    • 0000277551 scopus 로고
    • (a) For isolation of aspicilin see: Hesse, O. J. Prakt. Chem. 1900, 62, 430; 1904, 70, 449.
    • (1900) J. Prakt. Chem. , vol.62 , pp. 430
    • Hesse, O.1
  • 13
    • 0000277340 scopus 로고
    • (a) For isolation of aspicilin see: Hesse, O. J. Prakt. Chem. 1900, 62, 430; 1904, 70, 449.
    • (1904) J. Prakt. Chem. , vol.70 , pp. 449
  • 18
    • 0026317430 scopus 로고
    • For synthesis of 1 from (S)-methyloxirane, see: (b) Quinkert, G.; Heim, N.; Glenneberg, J.; Döller, U.; Eichhorn, M.; Billhardt, U.-M.; Schwarz, C.; Zimmermann, G.; Bats, J. W.; Dürner, G. Helv. Chim. Acta 1988, 71, 1719. (c) Quinkert, G.; Becker, H.; Dürner, G. Tetrahedron Lett. 1991, 32, 7397. (d) Oppolzer, W.; Radinov, R. N.; De Brabander, J. Tetrahedron Lett. 1995, 36, 2607.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 7397
    • Quinkert, G.1    Becker, H.2    Dürner, G.3
  • 19
    • 0028924320 scopus 로고
    • For synthesis of 1 from (S)-methyloxirane, see: (b) Quinkert, G.; Heim, N.; Glenneberg, J.; Döller, U.; Eichhorn, M.; Billhardt, U.-M.; Schwarz, C.; Zimmermann, G.; Bats, J. W.; Dürner, G. Helv. Chim. Acta 1988, 71, 1719. (c) Quinkert, G.; Becker, H.; Dürner, G. Tetrahedron Lett. 1991, 32, 7397. (d) Oppolzer, W.; Radinov, R. N.; De Brabander, J. Tetrahedron Lett. 1995, 36, 2607.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2607
    • Oppolzer, W.1    Radinov, R.N.2    De Brabander, J.3
  • 21
    • 0025771506 scopus 로고
    • For asymmetric synthesis of (-)-aspicilin utilizing a chiral sulfoxide group, see: (f) Solladié, G.; Fernandez, I.; Maestro, C. Tetrahedron: Asymmetry 1991, 2, 801. (g) For asymmetric synthesis of 1 via the SAMP/RAMP hydrazone technique, see: Enders, B.; Prokopenko, O. F. Liebigs Ann. 1995, 1185.
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 801
    • Solladié, G.1    Fernandez, I.2    Maestro, C.3
  • 22
    • 84988104072 scopus 로고
    • For asymmetric synthesis of (-)-aspicilin utilizing a chiral sulfoxide group, see: (f) Solladié, G.; Fernandez, I.; Maestro, C. Tetrahedron: Asymmetry 1991, 2, 801. (g) For asymmetric synthesis of 1 via the SAMP/RAMP hydrazone technique, see: Enders, B.; Prokopenko, O. F. Liebigs Ann. 1995, 1185.
    • (1995) Liebigs Ann. , pp. 1185
    • Enders, B.1    Prokopenko, O.F.2
  • 28
    • 8044252872 scopus 로고    scopus 로고
    • note
    • Considering a simple case of a molecule containing only two asymmetric centers which have four possible stereoisomers: RR, RS, SS, and SR, the epimeric excess at one center is defined as: epe = ([RR] + [RS]) - ([SS] + [SR])/[RR] + [RS] + [SS] + [SR]
  • 33
    • 8044248472 scopus 로고    scopus 로고
    • In comparison, the Quinkert synthesis of (+)-aspicilin from D-mannose (reference 12a) was achieved in 13% overall yield
    • In comparison, the Quinkert synthesis of (+)-aspicilin from D-mannose (reference 12a) was achieved in 13% overall yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.