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Volumn 38, Issue 20, 1999, Pages 3086-3089

High-yielding enantioselective synthesis of the macrolactam aglycon of Sch 38516 from two units of (2R)-2-ethyl-4-penten-1-ol

Author keywords

Aldol reactions; Antifungal agents; Asymmetric synthesis; Macrocycles; Total synthesis

Indexed keywords

2 ETHYL 4 PENTEN 1 OL; FLUVIRUCIN B1; LACTAM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033581623     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991018)38:20<3086::AID-ANIE3086>3.0.CO;2-D     Document Type: Article
Times cited : (18)

References (29)
  • 6
    • 0344692476 scopus 로고    scopus 로고
    • note
    • [1,2]
  • 12
    • 0030804229 scopus 로고    scopus 로고
    • [7) B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. 1997, 109, 1562- 1564; Angew. Chem. Int. Ed. 1997, 36, 1486-1489.
    • (1997) Angew. Chem. Int. Ed. , vol.36 , pp. 1486-1489
  • 14
    • 0038736789 scopus 로고
    • The auxiliaries of Evans et al. do not work with nonactivated substrates such as 9. The camphorsultam-derived auxiliary (W. Oppolzer, Tetrahedron 1987, 43, 1969-2004) afforded the desired alkylation product in only 39% yield, and, moreover, cleavage of the chiral auxiliary turned out to be troublesome.
    • (1987) Tetrahedron , vol.43 , pp. 1969-2004
    • Oppolzer, W.1
  • 16
    • 0030575394 scopus 로고    scopus 로고
    • For leading references on chiral boron enolates, see a) P. V. Ramachandran, W. Xu, H. C. Brown, Tetrahedron Lett. 1996, 37, 4911-4914; b) I. Paterson, K. R. Gibson, R. M. Oballa, Tetrahedron Lett. 1996, 37, 8584-8588.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4911-4914
    • Ramachandran, P.V.1    Xu, W.2    Brown, H.C.3
  • 17
    • 0345123186 scopus 로고    scopus 로고
    • For leading references on chiral boron enolates, see a) P. V. Ramachandran, W. Xu, H. C. Brown, Tetrahedron Lett. 1996, 37, 4911- 4914; b) I. Paterson, K. R. Gibson, R. M. Oballa, Tetrahedron Lett. 1996, 37, 8584-8588.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8584-8588
    • Paterson, I.1    Gibson, K.R.2    Oballa, R.M.3
  • 20
    • 84989581322 scopus 로고
    • b) C. Gennari, D. Moresca, S. Vieth, A. Vulpetti, Angew. Chem. 1993, 105, 1717-1719; Angew. Chem. Int. Ed. 1993, 32, 1618-1621;
    • (1993) Angew. Chem. Int. Ed. , vol.32 , pp. 1618-1621
  • 22
    • 0027724708 scopus 로고
    • 1H) values of the diastereomeric Mosher esters arising from (R)- and (S)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride (cf. I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092-4096).
    • (1993) Tetrahedron Lett. , vol.34 , pp. 8387-8390
    • Roush, W.R.1    Bannister, T.D.2    Wendt, M.D.3
  • 23
    • 2142858450 scopus 로고
    • 1H) values of the diastereomeric Mosher esters arising from (R)- and (S)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride (cf. I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092-4096).
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4092-4096
    • Ohtani, I.1    Kusumi, T.2    Kashman, Y.3    Kakisawa, H.4
  • 26
    • 0001486775 scopus 로고
    • For the reduction of azides with tin(II)-thiolate complexes, see a) M. Bartra, F. Urpí, J. Vilarrasa, Tetrahedron Lett. 1987, 28, 5941-5944; b) M. Bartra, P. Romea, F. Urpí, J. Vilarrasa, Tetrahedron 1990, 46, 587-594.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5941-5944
    • Bartra, M.1    Urpí, F.2    Vilarrasa, J.3
  • 27
    • 0000367997 scopus 로고
    • For the reduction of azides with tin(II)-thiolate complexes, see a) M. Bartra, F. Urpí, J. Vilarrasa, Tetrahedron Lett. 1987, 28, 5941-5944; b) M. Bartra, P. Romea, F. Urpí, J. Vilarrasa, Tetrahedron 1990, 46, 587-594.
    • (1990) Tetrahedron , vol.46 , pp. 587-594
    • Bartra, M.1    Romea, P.2    Urpí, F.3    Vilarrasa, J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.