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Volumn 38, Issue 6, 1997, Pages 1001-1004

Asymmetric synthesis of the C(18)-C(24) unit of lasonolide A

Author keywords

[No Author keywords available]

Indexed keywords

LASONOLIDE A; MACROLIDE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0031562078     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02481-1     Document Type: Article
Times cited : (41)

References (26)
  • 9
    • 0030574042 scopus 로고    scopus 로고
    • h) Sugasawa, K., Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377. Catalytic asymmetric alkylation. See: Imai, M.; Hagihara, H.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7377
    • Sugasawa, K.1    Shindo, M.2    Noguchi, H.3    Koga, K.4
  • 10
    • 0001266486 scopus 로고
    • h) Sugasawa, K., Shindo, M.; Noguchi, H.; Koga, K. Tetrahedron Lett. 1996, 37, 7377. Catalytic asymmetric alkylation. See: Imai, M.; Hagihara, H.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8829
    • Imai, M.H.H.1    Kawasaki, H.2    Manabe, K.3    Koga, K.4
  • 15
    • 0011288384 scopus 로고    scopus 로고
    • No attempts to recycle the α-configurated alcohol 4-α, e. g. by back oxidation to ketone 3 or by Mitsunobu inversion were made at this stage
    • 6. No attempts to recycle the α-configurated alcohol 4-α, e. g. by back oxidation to ketone 3 or by Mitsunobu inversion were made at this stage.
  • 16
    • 0000449913 scopus 로고
    • 7. Martin, S.F. Tetrahedron 1980, 36, 419; Fuji, K. Chem. Rev. 1993, 93, 2037.
    • (1980) Tetrahedron , vol.36 , pp. 419
    • Martin, S.F.1
  • 17
    • 0001521888 scopus 로고
    • 7. Martin, S.F. Tetrahedron 1980, 36, 419; Fuji, K. Chem. Rev. 1993, 93, 2037.
    • (1993) Chem. Rev. , vol.93 , pp. 2037
    • Fuji, K.1
  • 18
    • 0001399971 scopus 로고
    • and references cited therein
    • 8 Currently, four steps and even more per stereogenic centre are not uncommon in total synthesis of complex marine natural products. See: Norcross, R. D.; Paterson, J. Chem. Rev. 1995, 95, 2041 and references cited therein.
    • (1995) Chem. Rev. , vol.95 , pp. 2041
    • Norcross, R.D.1    Paterson, J.2
  • 21
    • 0028362496 scopus 로고
    • Previously, 8-oxabicyclo[3.2.1]octan-3-one, which is obtained from 1 by catalytic hydrogenation and is more stable, was desymmetrized with a chiral lithium amide base (ca, 78%, 82% e.e.; see ref. 2g)
    • c) Majewski, M.; Lazny, R. Tetrahedron Lett. 1994, 35, 3653. Previously, 8-oxabicyclo[3.2.1]octan-3-one, which is obtained from 1 by catalytic hydrogenation and is more stable, was desymmetrized with a chiral lithium amide base (ca, 78%, 82% e.e.; see ref. 2g).
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3653
    • Majewski, M.1    Lazny, R.2
  • 22
    • 0029118911 scopus 로고
    • Moreover, the classical problem of polyalkylation is circumvented with methyl cyanoformate
    • 3-hybridized electrophiles such as methyl halides and also benzyl halides give a poor yield of C-atkytation, which generally does not exceed 35-40%; cf. Rubinger, M. M. M.; Mann, J.; Drew, M. G. B. Tetrahedron 1995, 51, 11295. Moreover, the classical problem of polyalkylation is circumvented with methyl cyanoformate.
    • (1995) Tetrahedron , vol.51 , pp. 11295
    • Rubinger, M.M.M.1    Mann, J.2    Drew, M.G.B.3
  • 26
    • 0011378203 scopus 로고    scopus 로고
    • note
    • +, 11), 164 (21), 151 (23), 140 (25), 124 (20), 108 (24), 101 (61), 95 (12), 82 (100), 69 (66).


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