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Volumn 7, Issue 8, 2005, Pages 1589-1591

Enantioselective synthesis of the C18-C25 segment of lasonolide A by an oxonia-Cope Prins cascade

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; LASONOLIDE A; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 17844404230     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050270s     Document Type: Article
Times cited : (47)

References (33)
  • 9
    • 0030048549 scopus 로고    scopus 로고
    • For a related tetrahydropyran synthesis, see: (a) Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141-144. (b) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942-10953. (c) Cossey, K. N.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 12216-12217.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 141-144
    • Petasis, N.A.1    Lu, S.P.2
  • 10
    • 0035823867 scopus 로고    scopus 로고
    • For a related tetrahydropyran synthesis, see: (a) Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141-144. (b) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942-10953. (c) Cossey, K. N.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 12216-12217.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 10942-10953
    • Smith III, A.B.1    Minbiole, K.P.2    Verhoest, P.R.3    Schelhaas, M.4
  • 11
    • 4644259961 scopus 로고    scopus 로고
    • For a related tetrahydropyran synthesis, see: (a) Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141-144. (b) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942-10953. (c) Cossey, K. N.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 12216-12217.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 12216-12217
    • Cossey, K.N.1    Funk, R.L.2
  • 25
    • 17844409941 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of California, Irvine
    • (a) Hu, Yueqing, Ph.D. Thesis, University of California, Irvine, 1998.
    • (1998)
    • Hu, Y.1
  • 27
    • 0027376630 scopus 로고
    • (c) For a related example, see Mohr, P. Tetrahedron Lett. 1993, 34, 6251-6254.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6251-6254
    • Mohr, P.1
  • 31
    • 17844369263 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for details of the HPLC analysis of 10.
  • 32
    • 17844365677 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry of 19 was confirmed by COSY and NOESY studies. A NOESY correlation was observed between the C4-H and the C3-methyl group. There was no observed correlation between the C4-H and the C2 and C6 hydrogens, which showed enhancements to each other. The coupling constants for the C4-H (3.19 ppm; t, J = 2.9 Hz) combined with the NOESY data confirm that it is an equatorial proton.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.