메뉴 건너뛰기




Volumn 39, Issue 33, 1998, Pages 6037-6040

Studies in marine macrolide synthesis: Stereocontrolled synthesis of the C1-C11 and C15-C27 subunits of aplyronine A

Author keywords

[No Author keywords available]

Indexed keywords

APLYRONINE A; MACROLIDE; UNCLASSIFIED DRUG;

EID: 0032514418     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01191-5     Document Type: Article
Times cited : (31)

References (35)
  • 9
    • 0001790298 scopus 로고    scopus 로고
    • (c) For a review of boron-mediated aldol reactions, see: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
    • (1997) Org. React. , vol.51 , pp. 1
    • Cowden, C.J.1    Paterson, I.2
  • 10
    • 0010486888 scopus 로고    scopus 로고
    • note
    • 6. Ketone (R)-8 was prepared in 3 steps from methyl (R)-3-hydroxy-2-methylpropionate with the PMB protecting group introduced using PMBC(=NH)CCl3/TIOH (ref. 5, 19).
  • 13
    • 0010486889 scopus 로고    scopus 로고
    • note
    • 13C NMR δ (62.9 MHz, CDCl3) 202.8, 132.6, 131.6, 80.3, 76.7, 76.6, 63.6, 55.6, 50.9, 42.7, 39.0, 38.8, 34.1, 27.5, 27.3, 24.8, 21.6, 20.9, 20.4, 18.1, 15.2, 13.8, 11.9.
  • 15
    • 0010450669 scopus 로고    scopus 로고
    • note
    • 7.
  • 18
    • 0032546058 scopus 로고    scopus 로고
    • (b) Trost, B. M.; Kazmaier, U. J. Am. Chem. Soc. 1992, 114, 7933. See also Kazmaier, U. Tetrahedron 1998, 54, 1491.
    • (1998) Tetrahedron , vol.54 , pp. 1491
    • Kazmaier, U.1
  • 19
    • 0010450068 scopus 로고    scopus 로고
    • note
    • 12. The PMP acetal configuration in 4 and 13 was assigned based upon the nOe's indicated for i. (formula presented)
  • 20
    • 0029619410 scopus 로고
    • Selective removal of a PMB ether in the presence of a PMP acetal has been reported previously. For example, see: In contrast, our initial route to the aplyronines was revised because of the inability to deprotect the PMB ether in ii without reaction at the PMP acetal
    • 13. Selective removal of a PMB ether in the presence of a PMP acetal has been reported previously. For example, see: Smith, A. B. III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. In contrast, our initial route to the aplyronines was revised because of the inability to deprotect the PMB ether in ii without reaction at the PMP acetal.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 12011
    • Smith A.B. III1    Qiu, Y.2    Jones, D.R.3    Kobayashi, K.4
  • 31
    • 0025068753 scopus 로고
    • Use of the butyl oxazaborolidine and/or catecholborane as stoichiometric reductant did not improve the selectivity and lower yields resulted see Other asymmetric reducing agents such as those derived from LiA1H4 also proved unsatisfactory
    • 23. Use of the butyl oxazaborolidine and/or catecholborane as stoichiometric reductant did not improve the selectivity and lower yields resulted (see Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611). Other asymmetric reducing agents such as those derived from LiA1H4 also proved unsatisfactory.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 611
    • Corey, E.J.1    Bakshi, R.K.2
  • 33
    • 0028965619 scopus 로고
    • Precedent based on results in ref. 22(a) in conjunction with those of: (a)
    • 25. Precedent based on results in ref. 22(a) in conjunction with those of: (a) Bach, J.; Berenguer, R.; Garcia, J.; Vilarrasa, J. Tetrahedron 1995, 36, 3425.
    • (1995) Tetrahedron , vol.36 , pp. 3425
    • Bach, J.1    Berenguer, R.2    Garcia, J.3    Vilarrasa, J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.